Substituted benzene fungicides

ABSTRACT

Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, 
                         
wherein
         W is O or S;   V is a direct bond or NR 3 ;   Q is or CR 6a R 6b , O, NR 7 , C═N—O—R 7  or C(═O);   Y is —C(R 5 )═N—O—(CR 8a R 8b ) p —X—(CR 9a R 9b ) q —SiR 10a R 10b R 10c ; or a phenyl ring substituted as defined in the disclosure; or Z; and   R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9a , R 9b , R 10a , R 10b , R 10c , Z, p and q are as defined in the disclosure.
 
Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

This application is a division of application Ser. No. 12/593,360, filedSep. 28, 2009, which is a national stage entry of PCT/US2008/04443,filed Apr. 3, 2008. PCT/US2008/04443 claims priority benefit fromProvisional Application 61/008,425, filed Dec. 19, 2007, and fromProvisional Application 60/921,600, filed Apr. 3, 2007.

FIELD OF THE INVENTION

This invention relates to certain benzene fungicides, their N-oxides,salts and compositions, and methods of their use as fungicides.

BACKGROUND OF THE INVENTION

The control of plant diseases caused by fungal plant pathogens isextremely important in achieving high crop efficiency. Plant diseasedamage to ornamental, vegetable, field, cereal, and fruit crops cancause significant reduction in productivity and thereby result inincreased costs to the consumer. Many products are commerciallyavailable for these purposes, but the need continues for new compoundswhich are more effective, less costly, less toxic, environmentally saferor have different sites of action.

World Patent Publication WO 2001/010825 discloses certain carbamatederivatives of Formula i as fungicides.

wherein, inter alia, R¹ is C₁-C₆ alkyl; G is O, S or NR⁴; R² is H orC₁-C₆ alkyl; R³ is H or C₁-C₆ alkyl; X is halogen; n is 0 to 4; Q is Hor C₁-C₆ alkyl; and Y is C₁-C₁₀ alkyl.

World Patent Publication WO 2004/037770 discloses certainN-phenylhydrazine derivatives of Formula ii as fungicides andinsecticides.

wherein, inter alia, each R¹ and R² is independently H or C₁-C₆ alkyl;R³ is C₁-C₆ alkyl or C₁-C₆ alkoxy; R⁴ is H or halogen; R⁹ is H or C₁-C₆alkyl; and Y is H or C₁-C₆ alkyl.

World Patent publication WO 2005/051932 discloses certainarylheterocycle derivatives of Formula iii as fungicides andinsecticides.

wherein, inter alia, R₁ is C₁-C₆ alkyl or C₁-C₆ alkoxy; R₂ is halogen; mis 0 to 4; T is a substituted C—N or N—N bridge; and Q is aN-heterocycle also containing as ring members selected from O and S.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 (including allgeometric and stereoisomers), N-oxides, and salts thereof, agriculturalcompositions containing them and their use as fungicides:

wherein

-   -   each R¹ and R² is independently H, halogen, CN, C₁-C₃ alkyl,        C₁-C₃ alkoxy, C₁-C₃ haloalkyl, C₁-C₃ haloalkoxy, C₃-C₆        cycloalkyl, C₃-C₁₅ trialkylsilyl or C₃-C₁₅ halotrialkylsilyl;    -   V is a direct bond or NR³;    -   R³ is H, C₁-C₃ alkyl, C₃-C₆ cycloalkyl, C₁-C₃ haloalkyl, C₂-C₆        alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl or        C₂-C₆ haloalkoxycarbonyl;    -   R⁴ is H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkoxy, C₁-C₆ alkylamino,        C₁-C₆ haloalkylamino, C₂-C₈ dialkylamino, C₂-C₈ halodialkylamino        or C₃-C₆ cycloalkylamino;    -   W is O or S;    -   Q is CR^(6a)R^(6b), O, NR⁷, C(═N)—O—R⁷ or C(═O);    -   Y is        —C(R⁵)—N—O—(CR^(8a)R^(8b))_(p)—X—(CR^(9a)R^(9b))_(q)—SiR^(10a)R^(10b)R^(10c);        or Z; or a phenyl ring substituted with one substituent selected        from C₁-C₅ haloalkoxy, C₃-C₁₅ trialkylsilyl, C₃-C₁₅        halotrialkylsilyl, C₄-C₂₀ trialkylsilylalkyl, C₄-C₂₀        trialkylsilylalkoxy and C₅-C₂₅ trialkylsilylalkoxyalkyl and        optionally substituted with up to four additional substituents        independently selected from halogen, CN, C₁-C₃ alkyl, C₁-C₃        alkoxy, C₁-C₃ haloalkoxy, C₃-C₁₅ trialkylsilyl, C₃-C₁₅        halotrialkylsilyl, C₄-C₂₀ trialkylsilylalkyl, C₄-C₂₀        trialkylsilylalkoxy and C₅-C₂₅ trialkylsilylalkoxyalkyl;        provided that when Y is a phenyl ring, then Q is O, NR⁷,        C═N—O—R⁷ or C(═O);    -   Z is a 5- or 6-membered heteroaromatic ring selected from Z-1        through Z-24

-   -   R⁵ is H, CN, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl,        C₃-C₆ halocycloalkyl, C₃-C₁₅ trialkylsilyl or C₃-C₁₅        halotrialkylsilyl;    -   R^(6a) is H, OH, halogen, CN, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₂-C₆ alkoxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆        alkylsulfonyl;    -   R^(6b) is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkoxyalkyl,        C₁-C₆ alkoxy or C₁-C₆ haloalkoxy; or    -   R^(6a) and R^(6b) are taken together with the carbon atom to        which they are attached to form a C₃-C₆ cycloalkyl ring or C₃-C₆        halocycloalkyl ring;    -   R⁷ is H, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₂-C₃ alkylcarbonyl or        C₂-C₃ haloalkylcarbonyl;    -   each R^(8a) and R^(9a) is independently H, OH, CN, halogen,        C₁-C₅ alkyl, C₁-C₅ haloalkyl or C₁-C₅ alkoxy;    -   each R^(8b) and R^(9b) is independently H, CN, halogen, C₁-C₅        alkyl, C₁-C₅ haloalkyl or C₁-C₅ alkoxy; or    -   each pair of R^(8a) and R^(8b) or R^(9a) and R^(9b) attached to        the same carbon atom can be independently taken together with        the carbon atom to which they are attached to form a C₃-C₆        cycloalkyl or C₃-C₆ halocycloalkyl ring; or    -   each R^(8a), R^(8b), R^(9a) or R^(9b) can be independently taken        together with a R^(8a), R^(8b), R^(9a) or R^(9b) attached to an        adjacent carbon atom and the carbon atoms to which they are        attached to form a C₃-C₆ cycloalkyl or C₃-C₆ halocycloalkyl        ring;    -   each R^(10a), R^(10b) and R^(10c) is independently C₁-C₆ alkyl,        C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₈        alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₄-C₇        alkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₂-C₆ haloalkenyl,        C₁-C₆ alkylthio, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl,        C₄-C₁₂ trialkylsilylalkyl or J;    -   each J is independently a phenyl ring; a 5- or 6-membered        heteroaromatic ring; or an 8-, 9- or 10-membered fused bicyclic        ring system, or a 3- to 6-membered nonaromatic carbocyclic or        heterocyclic ring, said ring or ring system optionally including        ring members selected from the group consisting of C(═O), C(═S),        C(═NR¹¹), NR¹¹, SiR^(12a)R^(12b) and S(═O)_(u)(═NR¹¹)_(z), and        each ring or ring system optionally substituted with up to 5        substituents independently selected from R¹³; or    -   two of R^(10a), R^(10b) or R^(10c) are taken together with the        silicon atom to which they are attached to form a saturated ring        containing from 3 to 6 carbon atoms in addition to the silicon        atom as ring members, the ring optionally substituted on carbon        atoms with halogen;    -   X is a direct bond, O, NR¹¹, C(═O), C(═S) or C(═NR¹¹); or a        phenyl ring, a 5- or 6-membered heteroaromatic ring or a 3- to        8-membered nonaromatic carbocyclic or heterocyclic ring, said        ring optionally including ring members selected from the group        consisting of C(═O), C(═S), C(═NR¹¹), NR¹¹, SiR^(12a)R^(12b) and        S(═O)_(u)(═NR¹¹, and optionally substituted with up to 5        substituents independently selected from R¹³;    -   each R¹¹ is independently H, CN, NH₂, OH, C₁-C₆ alkyl, C₃-C₈        cycloalkyl, C₂-C₆ alkylcarbonyl, C₂-C₆ haloalkylcarbonyl or        C₁-C₆ alkoxy;    -   each R^(12a) and R^(12b) is independently C₁-C₅ alkyl, C₂-C₅        alkenyl, C₂-C₅ alkynyl, C₃-C₈ cycloalkyl, C₃-C₆ halocycloalkyl,        C₄-C₁₀ cycloalkylalkyl, C₄-C₇ alkylcycloalkyl, C₅-C₈        alkylcycloalkylalkyl, C₁-C₅ haloalkyl, C₁-C₅ alkoxy or C₁-C₅        haloalkoxy;    -   each R¹³ is independently halogen, C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₄-C₇        alkylcycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, cyano,        nitro, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylthio, C₁-C₆        haloalkylsulfinyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino,        C₂-C₆ dialkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl,        C₂-C₆ alkylaminocarbonyl, C₃-C₆ dialkylaminocarbonyl, C₃-C₁₅        trialkylsilyl or C₃-C₁₅ halotrialkylsilyl;    -   each R¹⁴ is independently H, halogen, cyano, hydroxy, amino,        nitro, —CH(═O) or —C(═O)NH₂; or C₁-C₆ alkyl, C₃-C₈ cycloalkyl,        C₃-C₆ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆        haloalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₂-C₈        alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy,        C₂-C₈ alkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₁-C₆        alkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        alkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈        dialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈ alkylcarbonylamino,        C₁-C₆ alkylsulfonylamino, C₁-C₆ alkylaminosulfonyl, C₂-C₈        dialkylaminosulfonyl, naphthalenyl or G^(A), each optionally        substituted with one or more substituents independently selected        from the group consisting of halogen, cyano, hydroxy, amino,        nitro, —CH(═O), —C(═O)OH, —C(═O)NH₂, —C(R¹⁵)═N—O—R¹⁶,        —C(R¹⁵)═N—R¹⁶, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈        alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀        cycloalkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy,        C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆        haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy,        C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₁-C₆        alkylthio, benzylthio, C₁-C₆ haloalkylthio, C₃-C₈        cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈        cycloalkylsulfonyl, C₃-C₁₀ trialkylsilyl, C₁-C₆ alkylamino,        C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈        halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈        alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆        alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino and G^(B);    -   G^(A) is independently a phenyl ring, benzyl, benzyloxy,        benzoyl, phenoxy or phenylsulfonyl or a 5- or 6-membered        heteroaromatic ring;    -   each G^(B) is independently a phenyl ring or a 5- or 6-membered        heteroaromatic ring optionally substituted with one or more        substituents independently selected from the group consisting of        halogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₃-C₆ halocycloalkyl, C₄-C₇ alkylcycloalkyl, C₁-C₆        haloalkyl, C₂-C₆ haloalkenyl, cyano, nitro, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy and C₁-C₆ alkylthio;    -   each R¹⁵ is H, C₁-C₃ alkyl, C₃-C₈ cycloalkyl or C₁-C₃ haloalkyl;    -   each R¹⁶ is H, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₂-C₃ alkylcarbonyl        or C₂-C₃ haloalkylcarbonyl;    -   m is an integer from 1 to 3;    -   p and q are independently an integer from 0 to 5; provided that        when p is 0, then X is other than O or NR¹¹; and    -   u and z in each instance of S(═O)_(u)(═NR¹¹)_(z) are        independently 0, 1 or 2, provided that the sum of u and z in        each instance of S(═O)_(u)(═NR¹¹)_(z) is 0, 1 or 2.

More particularly, this invention relates to a compound of Formula 1including all geometric and stereoisomers, an N-oxide or a salt thereof.

This invention also relates to a fungicidal composition comprising afungicidally effective amount of a compound of the invention and atleast one additional component selected from the group consisting ofsurfactants, solid diluents and liquid diluents.

This invention also relates to a fungicidal composition comprising (a) acompound of the invention and (b) at least one other fungicide (e.g., atleast one other fungicide having the same or different site of action).

This invention further relates to a method for controlling plantdiseases caused by fungal plant pathogens comprising applying to theplant or portion thereof, or to the plant seed, a fungicidally effectiveamount of a compound of the invention (e.g., as a composition describedherein).

DETAILS OF THE INVENTION

As used herein, the terms “comprises,” “comprising,” “includes,”“including,” “has,” “having”, “contains” or “containing” or any othervariation thereof, are intended to cover a non-exclusive inclusion. Forexample, a composition, process, method, article, or apparatus thatcomprises a list of elements is not necessarily limited to only thoseelements but may include other elements not expressly listed or inherentto such composition, process, method, article, or apparatus. Further,unless expressly stated to the contrary, “or” refers to an inclusive orand not to an exclusive or. For example, a condition A or B is satisfiedby any one of the following: A is true (or present) and B is false (ornot present), A is false (or not present) and B is true (or present),and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element orcomponent of the invention are intended to be nonrestrictive regardingthe number of instances (i.e. occurrences) of the element or component.Therefore “a” or “an” should be read to include one or at least one, andthe singular word form of the element or component also includes theplural unless the number is obviously meant to be singular.

As referred to in the present disclosure and claims, “plant” includesmembers of Kingdom Plantae, particularly seed plants (Spermatopsida), atall life stages, including young plants (e.g., germinating seedsdeveloping into seedlings) and mature, reproductive stages (e.g., plantsproducing flowers and seeds). Portions of plants include geotropicmembers typically growing beneath the surface of the growing medium(e.g., soil), such as roots, tubers, bulbs and corms, and also membersgrowing above the growing medium, such as foliage (including stems andleaves), flowers, fruits and seeds.

As referred to herein, the term “seedling”, used either alone or in acombination of words means a young plant developing from the embryo of aseed.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl”includes straight-chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkylene”denotes a straight-chain or branched alkanediyl. Examples of “alkylene”include CH₂, CH₂CH₂, CH(CH₃), CH₂CH₂CH₂, CH₂CH(CH₃) and the differentbutylene isomers.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.“Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of“alkoxyalkyl” include CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂and CH₃CH₂OCH₂CH₂. “Alkoxyalkoxy” denotes straight-chain or branchedalkoxy substitution on a straight-chain or branched alkoxy. Examples of“alkoxyalkoxy” include CH₃OCH₂O—, CH₃OCH₂(CH₃O)CHCH₂O— and(CH₃)₂CHOCH₂CH₂O—. “Alkenyloxy” includes straight-chain or branchedalkenyloxy moieties. Examples of “alkenyloxy” include H₂C═CHCH₂O,(CH₃)₂C═CHCH₂O, (CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O and CH₂═CHCH₂CH₂O.“Alkynyloxy” includes straight-chain or branched alkynyloxy moieties.Examples of “alkynyloxy” include HC—C≡CH₂O, CH₃C≡CCH₂O andCH₃C≡CCH₂CH₂O.

“Alkylthio” includes branched or straight-chain alkylthio moieties suchas methylthio, ethylthio, and the different propylthio, butylthio,pentylthio and hexylthio isomers. “Alkylsulfinyl” includes bothenantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl”include CH₃S(O)—, CH₃CH₂S(O)—, CH₃CH₂CH₂S(O)—, (CH₃)₂CHS(O)— and thedifferent butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.Examples of “Alkylsulfonyl” include CH₃S(O)₂—, CH₃CH₂S(O)₂—,CH₃CH₂CH₂S(O)₂—, (CH₃)₂CHS(O)₂—, and the different butylsulfonyl,pentylsulfonyl and hexylsulfonyl isomers. “Alkylamino” and“dialkylamino” and the like, are defined analogously to the aboveexamples.

“Trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicalsattached to and linked through a silicon atom, such as trimethylsilyl,triethylsilyl and tert-butyldimethylsilyl.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution ona cycloalkyl moiety and includes, for example, ethylcyclopropyl,i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term“cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety.Examples of “cycloalkylalkyl” include cyclopropylmethyl,cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chainor branched alkyl groups.

The term “cycloalkoxy” denotes cycloalkyl linked through an oxygen atomsuch as cyclopentyloxy and cyclohexyloxy. “Cycloalkylalkoxy” denotescycloalkylalkyl linked through an oxygen atom. Examples of“cycloalkylalkoxy” include cyclopropylmethoxy, cyclopentylethoxy, andother cycloalkyl moieties bonded to straight-chain or branched alkoxygroups.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moietiesbonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH₃C(═O)—,CH₃CH₂CH₂C(═O)— and (CH₃)₂CHC(═O)—. Examples of “alkoxycarbonyl” includeCH₃C(═O)—, CH₃CH₂OC(═O)—, CH₃CH₂CH₂C(═O)—, (CH₃)₂CHOC(═O)— and thedifferent butoxy- or pentoxycarbonyl isomers. Examples of“alkylaminocarbonyl” include CH₃NHC(═O)—, CH₃CH₂NHC(═O)—,CH₃CH₂CH₂NHC(═O)—, (CH₃)₂CHNHC(═O)— and the different butylamino- orpentylaminocarbonyl isomers. Examples of “dialkylaminocarbonyl” include(CH₃)₂NC(═O)—, (CH₃CH₂)₂NC(═O)—, CH₃CH₂(CH₃)NC(═O)—,(CH₃)₂CHN(CH₃)C(═O)— and CH₃CH₂CH₂(CH₃)NC(═O)—.

“Cycloalkylamino” denotes cycloalkyl linked through an amine group suchas cyclopropylamino, cyclobutylamino, cyclopentylamino andcyclohexylamino.

The term “halogen”, either alone or in compound words such as“haloalkyl”, or when used in descriptions such as “alkyl substitutedwith halogen” includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, or when used indescriptions such as “alkyl substituted with halogen” said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” or “alkyl substituted withhalogen” include F₃C—, ClCH₂, CF₃CH₂— and CF₃CCl₂—. The terms“halocycloalkyl”, “haloalkoxy”, “haloalkylthio”, “haloalkenyl”,“haloalkenyloxy” and “haloalkynyloxy” and the like, are definedanalogously to the term “haloalkyl”. Examples of “haloalkoxy” includeCF₃O—, CCl₃CH₂O—, HCF₂CH₂CH₂O— and CF₃CH₂O—. Examples of “haloalkylthio”include CCl₃S—, CF₃S—, CCl₃CH₂S— and ClCH₂CH₂CH₂S—. Examples of“haloalkylsulfinyl” include CF₃S(O)—, CCl₃S(O)—, CF₃CH₂S(O)— andCF₃CF₂S(O)—. Examples of “haloalkylsulfonyl” include CF₃S(O)₂—,CCl₃S(O)₂—, CF₃CH₂S(O)₂— and CF₃CF₂S(O)₂—. Examples of “haloalkenyl”include (Cl)₂C═CHCH₂— and CF₃CH₂CH═CHCH₂—. Examples of“halodialkylamino” include CF₃(CH₃)N—, (CF₃)₂N— and CH₂Cl(CH₃)N.Examples of “halotrialkylsilyl” include CF₃(CH₃)₂Si—, (CF₃)₃Si—, andCH₂Cl(CH₃)₂Si—.

The abbreviation “CN” means cyano.

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are integers from 1 to 25. Forexample, C₁-C₄ alkylsulfonyl designates methylsulfonyl throughbutylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂—; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃)—, CH₃OCH₂CH₂— or CH₃CH₂OCH₂—; andC₄ alkoxyalkyl designates the various isomers of an alkyl groupsubstituted with an alkoxy group containing a total of four carbonatoms, examples including CH₃CH₂CH₂OCH₂— and CH₃CH₂OCH₂CH₂—.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents, e.g., —(CR^(8a)R^(8b))_(p)—, p is 1, 2,3, 4 or 5. Further, when the subscript indicates a range, e.g.(R)_(i-j), then the number of substituents may be selected from theintegers between i and j inclusive. When one or more positions on agroup are said to be “not substituted” or “unsubstituted”, then hydrogenatoms are attached to take up any free valency.

Unless otherwise indicated, a “ring” or “ring system” as a component ofFormula 1 (e.g., substituent J) is carbocyclic or heterocyclic. The term“ring system” denotes two or more fused rings. The terms “bicyclic ringsystem” and “fused bicyclic ring system” denote a ring system consistingof two fused rings, in which either ring can be saturated, partiallyunsaturated, or fully unsaturated unless otherwise indicated. The term“ring member” refers to an atom (e.g., C, O, N or S) or other moiety(e.g., C(═O), C(═S), S(O) or S(O)₂) forming the backbone of a ring orring system.

The terms “carbocyclic ring”, “carbocycle” or “carbocyclic ring system”denote a ring or ring system wherein the atoms forming the ring backboneare selected only from carbon. Unless otherwise indicated, a carbocyclicring can be a saturated, partially unsaturated, or fully unsaturatedring. When a fully unsaturated carbocyclic ring satisfies Hückel's rule,then said ring is also called an “aromatic ring”. “Saturatedcarbocyclic” refers to a ring having a backbone consisting of carbonatoms linked to one another by single bonds; unless otherwise specified,the remaining carbon valences are occupied by hydrogen atoms.

The terms “heterocyclic ring”, “heterocycle” or “heterocyclic ringsystem” denote a ring or ring system in which at least one atom formingthe ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur.Typically a heterocyclic ring contains no more than 4 nitrogens, no morethan 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, aheterocyclic ring can be a saturated, partially unsaturated, or fullyunsaturated ring. When a fully unsaturated heterocyclic ring satisfiesHiickel's rule, then said ring is also called a “heteroaromatic ring” or“aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclicrings and ring systems can be attached through any available carbon ornitrogen by replacement of a hydrogen on said carbon or nitrogen.

“Aromatic” indicates that each of the ring atoms is essentially in thesame plane and has a p-orbital perpendicular to the ring plane, and inwhich (4n+2) π electrons, where n is a positive integer, are associatedwith the ring to comply with Hiickel's rule. The term “aromatic ringsystem” denotes a carbocyclic or heterocyclic ring system in which atleast one ring of the ring system is aromatic. The term “aromaticcarbocyclic ring system” denotes a carbocyclic ring system in which atleast one ring of the ring system is aromatic.

The term “aromatic heterocyclic ring system” denotes a heterocyclic ringsystem in which at least one ring of the ring system is aromatic. Theterm “nonaromatic ring system” denotes a carbocyclic or heterocyclicring system that may be fully saturated, as well as partially or fullyunsaturated, provided that none of the rings in the ring system arearomatic.

The term “optionally substituted” in connection with R^(10a), R^(10b),R^(10c), R¹⁴, G^(B), J and X refers to groups which are unsubstituted orhave at least one non-hydrogen substituent that does not extinguish thebiological activity possessed by the unsubstituted analog. As usedherein, the following definitions shall apply unless otherwiseindicated. The term “optionally substituted” is used interchangeablywith the phrase “substituted or unsubstituted” or with the term“(un)substituted.” Unless otherwise indicated, an optionally substitutedgroup may have a substituent at each substitutable position of thegroup, and each substitution is independent of the other. Commonly, thenumber of optional substituents (when present) ranges from 1 to 3. Whena range specified for the number of substituents (e.g., r being aninteger from 0 to 4 in Exhibit 1) exceeds the number of positionsavailable for substituents on a ring (e.g., 1 position available for(R^(v))_(r) on U-29 in Exhibit 3), the actual higher end of the range isrecognized to be the number of available positions. The term “optionallysubstituted” means that the number of substituents can be zero. Forexample, the phrase “optionally substituted with up to 5 substituentsindependently selected from R¹³” means that 0, 1, 2, 3, 4 or 5substituents can be present (if number of potential connection pointsallows), and thus the number of R¹³ substituents can be zero.

When J is a 3- to 6-membered nitrogen-containing heterocyclic ring, itmay be attached to the remainder of Formula 1 though any availablecarbon or nitrogen ring atom, unless otherwise described.

As noted above, J can be (among others) a phenyl ring optionallysubstituted with one or more substituents selected from a group ofsubstituents as defined in the Summary of Invention (i.e. R¹³). Anexample of a phenyl ring optionally substituted with up to 5substituents is the ring illustrated as U-1 in Exhibit 1, wherein R^(v)is R¹³ as defined in the Summary of the Invention for J and r is aninteger from 0 to 5. Also, as noted above, J can be (among others) a 5-or 6-membered heteroaromatic ring, optionally substituted with one ormore substituents selected from a group of substituents as defined inthe Summary of Invention. Examples of a 5- or 6-membered heteroaromaticring optionally substituted with from one or more substituents includethe rings U-2 through U-61 illustrated in Exhibit 1 wherein R^(v) is anysubstituent as defined in the Summary of the Invention for J (i.e. R¹³)and r is an integer from 0 to 4, limited by the number of availablepositions on each U group. As U-29, U-30, U-36, U-37, U-38, U-39, U-40,U-41, U-42 and U-43 have only one available position, for these U groupsr is limited to the integers 0 or 1, and r being 0 means that the Ugroup is unsubstituted and a hydrogen is present at the positionindicated by (R^(V))_(r).

Exhibit 1

Examples of a 5- or 6-membered nonaromatic unsaturated heterocyclic ringinclude the rings G-1 through G-35 as illustrated in Exhibit 2, whereinin R^(v) is R¹³ as defined in the Summary of the Invention. The optionalsubstituents corresponding to R^(v) can be attached to any availablecarbon or nitrogen by replacing a hydrogen atom. For these G rings, r istypically an integer from 0 to 4, limited by the number of availablepositions on each G group. Note that when the attachment point on the Ggroup is illustrated as floating, the G group can be attached to theremainder of Formula 1 through any available carbon or nitrogen of the Ggroup by replacement of a hydrogen atom.

Note that when J comprises a ring selected from G-28 through G-35, G² isselected from O, S and N. Note that when G² is N, the nitrogen atom cancomplete its valence by substitution with either H or the substituentscorresponding to R^(v) as defined in the Summary of Invention for J(i.e. R¹³).

Exhibit 2

As noted above, J can be (among others) an 8-, 9- or 10-membered fusedbicyclic ring system optionally substituted with one or moresubstituents selected from a group of substituents as defined in theSummary of Invention (i.e. R¹³). Examples of 8-, 9- or 10-membered fusedbicyclic ring system optionally substituted with up to 5 substituentsinclude the rings U-81 through U-123 illustrated in Exhibit 3 whereinR^(v) is any substituent as defined in the Summary of the Invention forJ (i.e. R¹³), and r is typically an integer from 0 to 5.

Exhibit 3

Although R^(v) groups are shown in the structures U-1 through U-123, itis noted that they do not need to be present since they are optionalsubstituents. The nitrogen atoms that require substitution to fill theirvalence are substituted with H or R^(v). Note that when the point ofattachment between (R^(v))_(r) and the U group is illustrated asfloating, (R^(v))_(r) can be attached to any available carbon atom ornitrogen atom of the U group. Note that when the attachment point on theU group is illustrated as floating, the U group can be attached to theremainder of Formula 1 through any available carbon or nitrogen of the Ugroup by replacement of a hydrogen atom. Note that some U groups canonly be substituted with less than 4 R^(v) groups (e.g., U-2 throughU-5, U-7 through U-48, and U-52 through U-61).

A wide variety of synthetic methods are known in the art to enablepreparation of aromatic and nonaromatic heterocyclic rings and ringsystems; for extensive reviews see the eight volume set of ComprehensiveHeterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief,Pergamon Press, Oxford, 1984 and the twelve volume set of ComprehensiveHeterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V.Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. One skilled in the art will appreciate that onestereoisomer may be more active and/or may exhibit beneficial effectswhen enriched relative to the other stereoisomer(s) or when separatedfrom the other stereoisomer(s). Additionally, the skilled artisan knowshow to separate, enrich, and/or to selectively prepare saidstereoisomers. The compounds of the invention may be present as amixture of stereoisomers, individual stereoisomers or as an opticallyactive form.

One skilled in the art will appreciate that not all nitrogen-containingheterocycles can form N-oxides since the nitrogen requires an availablelone pair for oxidation to the oxide; one skilled in the art willrecognize those nitrogen-containing heterocycles which can formN-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and m-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding nonsalt forms, salts share thebiological utility of the nonsalt forms. Thus a wide variety of salts ofthe compounds of Formula 1 are useful for control of plant diseasescaused by fungal plant pathogens (i.e. are agriculturally suitable). Thesalts of the compounds of Formula 1 include acid-addition salts withinorganic or organic acids such as hydrobromic, hydrochloric, nitric,phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic,oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valericacids. When a compound of Formula 1 contains an acidic moiety such as acarboxylic acid or phenol, salts also include those formed with organicor inorganic bases such as pyridine, triethylamine or ammonia, oramides, hydrides, hydroxides or carbonates of sodium, potassium,lithium, calcium, magnesium or barium. Accordingly, the presentinvention comprises compounds selected from Formula 1, N-oxides andagriculturally suitable salts thereof.

Embodiments of the present invention as described in the Summary of theInvention include (where Formula 1 as used in the following Embodimentsincludes N-oxides and salts thereof):

Embodiment 1

A compound of Formula 1 wherein R¹ is H, halogen, CN, C₁-C₃ alkyl, C₁-C₃alkoxy, C₁-C₃ haloalkyl, C₁-C₃ haloalkoxy, C₃-C₄ cycloalkyl, C₃-C₆trialkylsilyl or C₃-C₆ halotrialkylsilyl.

Embodiment 1a

A compound of Embodiment 1 wherein R¹ is halogen, CN, C₁-C₂ alkyl, C₁-C₂alkoxy, C₁-C₂ haloalkyl or C₁-C₂ haloalkoxy.

Embodiment 1b

A compound of Embodiment 1a wherein R¹ is halogen, CN, C₁-C₂ alkyl orC₁-C₂ haloalkyl.

Embodiment 1c

A compound of Embodiment 1b wherein R¹ is F, Cl, Br, CN, methyl or C₁haloalkyl.

Embodiment 1d

A compound of Embodiment 1c wherein R¹ is Cl or methyl.

Embodiment 2

A compound of Formula 1 wherein R² is H, halogen, CN, C₁-C₃ alkyl, C₁-C₃alkoxy or C₁-C₃ haloalkyl.

Embodiment 2a

A compound of Embodiment 2 wherein R² is H, halogen, CN, methyl ortrifluoromethyl.

Embodiment 2b

A compound of Embodiment 2a wherein R² is H or halogen.

Embodiment 2c

A compound of Embodiment 2b wherein R² is H, F or Cl.

Embodiment 2d

A compound of Embodiment 2c wherein R² is H.

Embodiment 3

A compound of Formula 1 wherein R³ is H, C₁-C₂ alkyl, C₁-C₂ haloalkyl,C₂-C₃ alkylcarbonyl or C₂-C₃ haloalkylcarbonyl.

Embodiment 3a

A compound of Embodiment 3 wherein R³ is H, C₁-C₂ alkyl or C₁-C₂haloalkyl.

Embodiment 3b

A compound of Embodiment 3a wherein R³ is H.

Embodiment 4

A compound of Formula 1 wherein R⁴ is C₁-C₂ alkoxy, C₁-C₂ haloalkoxy,C₃-C₄ cycloalkoxy, C₁-C₂ alkylamino, C₁-C₂ haloalkylamino, C₂-C₄dialkylamino, C₂-C₄ halodialkylamino or C₃-C₄ cycloalkylamino.

Embodiment 4a

A compound of Embodiment 4 wherein R⁴ is C₁-C₂ alkoxy, C₁-C₂ haloalkoxy,C₁-C₂ alkylamino or C₂-C₄ dialkylamino.

Embodiment 4b

A compound of Embodiment 4a wherein R⁴ is C₁-C₂ alkoxy or C₁-C₂haloalkoxy.

Embodiment 4c

A compound of Embodiment 4b wherein R⁴ is methoxy.

Embodiment 5

A compound of Formula 1 wherein W is O.

Embodiment 6

A compound of Formula 1 wherein W is S.

Embodiment 7

A compound of Formula 1 wherein Q is CR^(6a)R^(6b), O, NR⁷ or C═N—O—R⁷.

Embodiment 7a

A compound of Formula 1 wherein Q is CR^(6a)R^(6b) or NR⁷.

Embodiment 7b

A compound of Formula 1 wherein Q is O or NR⁷.

Embodiment 7c

A compound of Formula 1 wherein Q is CR^(6a)R^(6b).

Embodiment 7d

A compound of Formula 1 wherein Q is NR⁷.

Embodiment 7e

A compound of Formula 1 wherein Q is C═N—O—R⁷.

Embodiment 7f

A compound of Formula 1 wherein R^(6a) and R^(6b) are independently H,halogen, CN, C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 7g

A compound of Embodiment 7f wherein R^(6a) and R^(6b) are independentlyH, F, CN or methyl.

Embodiment 7h

A compound of Embodiment 7g wherein R^(6a) and R^(6b) are H.

Embodiment 8

A compound of Formula 1 wherein R⁷ is H, C₁-C₂ alkyl, C₁-C₂ haloalkyl,C₂-C₃ alkylcarbonyl or C₂-C₃ haloalkylcarbonyl.

Embodiment 9

A compound of Embodiment 8 wherein R⁷ is H, methyl, C₁-C₃ haloalkyl,acetyl or haloacetyl.

Embodiment 10

A compound of Embodiment 9 wherein R⁷ is H.

Embodiment 11

A compound of Formula 1 wherein Y is—C(R⁵)—N—O—(CR^(8a)R^(8b))_(p)—X—(CR^(9a)R^(9b))_(q)SiR^(10a)R^(10b)R^(10c).

Embodiment 11a

A compound of Formula 1 wherein p is 0.

Embodiment 12

A compound of Formula 1 wherein Y is a phenyl ring substituted with onesubstituent selected from C₁-C₅ haloalkoxy, C₃-C₁₅ trialkylsilyl, C₃-C₁₅halotrialkylsilyl, C₄-C₂₀ trialkylsilylalkyl, C₄-C₂₀ trialkylsilylalkoxyand C₅-C₂₅ trialkylsilylalkoxyalkyl and optionally substituted with upto four additional substituents independently selected from halogen, CN,C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₃-C₁₅ trialkylsilyl,C₃-C₁₅ halotrialkylsilyl, C₄-C₂₀ trialkylsilylalkyl, C₄-C₂₀trialkylsilylalkoxy and C₅-C₂₅ trialkylsilylalkoxyalkyl.

Embodiment 13

A compound of Embodiment 12 wherein Y is a phenyl ring substituted withone additional substituent selected from C₁-C₃ haloalkoxy, C₃-C₉trialkylsilyl, C₃-C₉ halotrialkylsilyl, C₄-C₁₂ trialkylsilylalkyl andC₄-C₁₂ trialkylsilylalkoxy, and optionally substituted with up to fouradditional substituents independently selected from halogen, CN, C₁-C₃alkyl, C₁-C₃ alkoxy and C₁-C₃ haloalkoxy.

Embodiment 14

A compound of Embodiment 13 wherein Y is a phenyl ring substituted withone additional substituent selected from C₁-C₃ haloalkoxy or C₃-C₆trialkylsilyl, and optionally substituted with up to four additionalsubstituents independently selected from halogen and C₁-C₃ alkyl.

Embodiment 15

A compound of Embodiment 14 wherein Y is a phenyl ring substituted withone additional substituent selected from C₁-C₃ haloalkoxy and C₃-C₆trialkylsilyl.

Embodiment 16

A compound of Formula 1 wherein Y is Z.

Embodiment 16a

A compound of Embodiment 16 wherein Z is Z-1, Z-2, Z-3, Z-4, Z-6, Z-7,Z-8, Z-9, Z-11, Z-12, Z-18 or Z-24.

Embodiment 16b

A compound of Embodiment 16a wherein each R¹⁴ is independently halogen,C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₁-C₆ haloalkyl, C₁-C₆ haloalkoxy, orG^(A) each optionally substituted with one or more substituentsindependently selected from the group halogen, cyano, hydroxy, amino,nitro, —CH(═O), —C(═O)OH, —C(═O)NH₂, C(R¹⁵)═N—O—R¹⁶, C(R¹⁵)—N—R¹⁶, C₁-C₆alkyl, C₃-C₈ cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,C₂-C₈ alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈cycloalkoxy and C₃-C₁₀ trialkylsilyl.

Embodiment 16c

A compound of Embodiment 16b wherein each G^(A) is independently phenyl,benzyl or 5- or 6-membered heteroaromatic ring, each optionallysubstituted with one or more substituents independently selected fromthe group halogen, —CH(═O), —C(R¹⁵)═N—O—R¹⁶, C(R¹⁵)═N—R¹⁶, C₁-C₆ alkyl,C₃-C₈ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆ alkoxy,C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy and C₃-C₁₀ trialkylsilyl.

Embodiment 16d

A compound of Embodiment 16c wherein each G^(A) is independently phenylor 1,2,4-thiadiazole each optionally substituted with one or moresubstituents independently selected from the group halogen, C₁-C₆ alkyl,C₃-C₈ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy andC₃-C₁₀ trialkylsilyl.

Embodiment 16e

A compound of Embodiment 16a wherein Q is CR^(6a)R^(6b).

Embodiment 17

A compound of Formula 1 wherein R⁵ is C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 17a

A compound of Embodiment 17 wherein R⁵ is C₁-C₃ alkyl.

Embodiment 17b

A compound of Embodiment 17a wherein R⁵ is methyl.

Embodiment 18

A compound of Embodiment 17 wherein R⁵ is C₁-C₃ haloalkyl.

Embodiment 19

A compound of Formula 1 wherein p and q are independently an integerfrom 0 to 3.

Embodiment 20

A compound of Formula 1 wherein each R^(8a) and R^(9a) is independentlyH, OH, CN, halogen, C₁-C₅ alkyl, C₁-C₅ haloalkyl or C₁-C₅ alkoxy.

Embodiment 21

A compound of Embodiment 20 wherein each R^(8a) and R^(9a) isindependently H, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl or C₁-C₃ alkoxy.

Embodiment 22

A compound of Formula 1 wherein each R^(10a), R^(10b) and R^(10c) isindependently C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₈ alkoxyalkyl, C₂-C₈haloalkoxyalkyl, C₃-C₆ cycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl or J.

Embodiment 22a

A compound of Formula 1 wherein J is independently a phenyl ring, or a5- or 6-membered heteroaromatic ring, or a 3- to 6-membered nonaromaticcarbocyclic or heterocyclic ring, each optionally including ring membersselected from the group consisting of C(═O), C(═S), C(═NR¹¹), NR¹¹,SiR^(12a)R^(12b) and S(═O)_(u)(═NR¹¹)_(z); each ring optionallysubstituted with up to 5 substituents independently selected from R¹³.

Embodiment 23

A compound of Embodiment 22 wherein each R^(10a), R^(10b) and R^(10c) isindependently C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₈ alkoxyalkyl, C₂-C₈haloalkoxyalkyl, C₃-C₆ cycloalkyl or C₅-C₁₀ alkylcycloalkylalkyl.

Embodiment 24

A compound of Formula 1 wherein X is a direct bond, O or C(═O); or aphenyl ring; or a 5- or 6-membered heteroaromatic ring or a 3- to6-membered nonaromatic carbocyclic or heterocyclic ring, each optionallyincluding ring members selected from the group consisting of C(═O),C(═S), C(═NR¹¹), NR¹¹, SiR^(12a)R^(12b) or S(O)_(u)(═NR¹¹)_(z); eachring optionally substituted with up to 3 substituents independentlyselected from R¹³.

Embodiment 24a

A compound of Formula 1 wherein X is a direct bond.

Embodiment 25

A compound of Formula 1 wherein each R¹¹ is independently H, CN, C₁-C₆alkyl, C₃-C₁₀ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆haloalkylcarbonyl.

Embodiment 26

A compound of Formula 1 wherein each R^(12a) and R^(12b) isindependently C₁-C₅ alkyl or C₁-C₅ haloalkyl.

Embodiment 27

A compound of Formula 1 wherein each R¹³ is independently halogen, C₁-C₆alkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₄-C₇ alkylcycloalkyl,C₁-C₆ haloalkyl, cyano, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio,C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl orC₃-C₆ dialkylaminocarbonyl.

Embodiment 28

A compound of Embodiment 27 wherein each R¹³ is independently halogen,C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, cyano, C₁-C₆ alkoxy, orC₁-C₆ haloalkoxy.

Embodiment 29

A compound of Formula 1 wherein V is NR³.

Embodiment 30

A compound of Formula 1 wherein V is a direct bond and Q C(═N)—O—R⁷ orC(═O).

Embodiment 31

A compound of Formula 1 wherein

V is other than a direct bond;

R³ and R⁴ are other than C₃-C₆ cycloalkyl;

R⁵ is other than C₃-C₆ halocycloalkyl;

Q is other than C═N—O—R⁷;

Y is other than Z; and

R¹⁴ is other than C₃-C₆ halocycloalkyl, C₁-C₆ haloalkyl, C₁-C₆haloalkoxy, C₃-C₈ halocycloalkoxy.

Embodiment 32

A compound of Formula 1 wherein

V is other than a direct bond;

R⁵ is other than C₃-C₆ halocycloalkyl; and

R¹⁴ is other than C₃-C₆ halocycloalkyl, C₁-C₆ haloalkyl, C₁-C₆haloalkoxy, C₃-C₈ halocycloalkoxy.

Embodiments of this invention, including Embodiments 1-32 above as wellas any other embodiments described herein, can be combined in anymanner, and the descriptions of variables in the embodiments pertain notonly to the compounds of Formula 1 but also to the starting compoundsand intermediate compounds useful for preparing the compounds ofFormula 1. In addition, embodiments of this invention, includingEmbodiments 1-32 above as well as any other embodiments describedherein, and any combination thereof, pertain to the compositions andmethods of the present invention.

Combinations of Embodiments 1-32 are illustrated by:

Embodiment A

A compound of Formula 1 wherein

-   -   R¹ is halogen, CN, C₁-C₂ alkyl, C₁-C₂ alkoxy, C₁-C₂ haloalkyl,        or C₁-C₂ haloalkoxy;    -   R² is H, halogen, CN, methyl or trifluoromethyl;    -   V is NR³;    -   R³ is H, C₁-C₂ alkyl, C₁-C₂ haloalkyl, C₂-C₃ alkylcarbonyl or        C₂-C₃ haloalkylcarbonyl;    -   R⁴ is C₁-C₂ alkoxy, C₁-C₂ haloalkoxy, C₁-C₂ alkylamino or C₂-C₄        dialkylamino;    -   W is O;    -   Q is CR^(6a)R^(6b), C═N—O—R⁷, O or NR⁷;

R⁵ is C₁-C₃ alkyl or C₁-C₃ haloalkyl; and

Y is—C(R⁵)═N—O—(CR^(8a)R^(8b))_(p)—X—(CR^(9a)R^(9b))_(q)—SiR^(10a)R^(10b)R^(10c).

Embodiment A1

A compound of Embodiment A wherein

-   -   R¹ is F, Cl, Br, CN, methyl or C₁ haloalkyl;    -   R² is H, F or Cl;    -   R³ is H, C₁-C₂ alkyl or C₁-C₂ haloalkyl;    -   R⁴ is C₁-C₂ alkoxy or C₁-C₂ haloalkoxy;    -   Q is CR^(6a)R^(6b) or NR⁷;    -   R⁵ is C₁-C₃ alkyl;    -   p is 0; and    -   X is direct bond.

Embodiment A2

A compound of Embodiment A1 wherein

-   -   R¹ is Cl or methyl;    -   R² is H;    -   R³ is H;    -   R⁴ is methoxy;    -   Q is CR^(6a)R^(6b); and    -   R⁵ is methyl.

Embodiment B

A compound of Formula 1 wherein

-   -   R¹ is halogen, CN, C₁-C₂ alkyl, C₁-C₂ alkoxy, C₁-C₂ haloalkyl or        C₁-C₂ haloalkoxy;    -   R² is H, halogen, CN, methyl or trifluoromethyl;    -   V is NR³;    -   R³ is H, C₁-C₂ alkyl, C₁-C₂ haloalkyl, C₂-C₃ alkylcarbonyl or        C₂-C₃ haloalkylcarbonyl;    -   R⁴ is C₁-C₂ alkoxy, C₁-C₂ haloalkoxy, C₁-C₂ alkylamino or C₂-C₄        dialkylamino;    -   W is O;    -   Q is O or NR⁷; and    -   Y is a phenyl ring substituted with one substituent selected        from C₁-C₅ haloalkoxy, C₃-C₁₅ trialkylsilyl, C₃-C₁₅        halotrialkylsilyl, C₄-C₂₀ trialkylsilylalkyl, C₄-C₂₀        trialkylsilylalkoxy and C₅-C₂₅ trialkylsilylalkoxyalkyl and        optionally substituted with up to four additional substituents        independently selected from halogen, CN, C₁-C₃ alkyl, C₁-C₃        alkoxy, C₁-C₃ haloalkoxy, C₃-C₁₅ trialkylsilyl, C₃-C₁₅        halotrialkylsilyl, C₄-C₂₀ trialkylsilylalkyl, C₄-C₂₀        trialkylsilylalkoxy and C₅-C₂₅ trialkylsilylalkoxyalkyl.

Embodiment B1

A compound of Embodiment B wherein

-   -   R¹ is halogen, CN, C₁-C₂ alkyl or C₁-C₂ haloalkyl;    -   R² is H or halogen;    -   R³ is H, C₁-C₂ alkyl or C₁-C₂ haloalkyl;    -   R⁴ is C₁-C₂ alkoxy or C₁-C₂ haloalkoxy;    -   Q is NR⁷;    -   R⁵ is C₁-C₃ alkyl; and    -   Y is a phenyl ring substituted with one additional substituent        selected from C₁-C₃ haloalkoxy, C₃-C₉ trialkylsilyl, C₃-C₉        halotrialkylsilyl, C₄-C₁₂ trialkylsilylalkyl and C₄-C₁₂        trialkylsilylalkoxy, and optionally substituted with up to four        additional substituents independently selected from halogen, CN,        C₁-C₃ alkyl, C₁-C₃ alkoxy and C₁-C₃ haloalkoxy.

Embodiment B2

A compound of Embodiment B1 wherein

-   -   R¹ is Cl or methyl;    -   R² is H;    -   R³ is H;    -   R⁴ is methoxy;    -   R⁵ is methyl; and    -   Y is a phenyl ring with one substituent selected from C₁-C₃        haloalkoxy and C₃-C₆ trialkylsilyl.

Embodiment C

A compound of Formula 1 wherein

-   -   R¹ is halogen, CN, C₁-C₂ alkyl, C₁-C₂ alkoxy, C₁-C₂ haloalkyl or        C₁-C₂ haloalkoxy;    -   R² is H, halogen, CN, methyl or trifluoromethyl;    -   R³ is H, C₁-C₂ alkyl, C₁-C₂ haloalkyl, C₂-C₃ alkylcarbonyl or        C₂-C₃ haloalkylcarbonyl;    -   R⁴ is C₁-C₂ alkoxy, C₁-C₂ haloalkoxy, C₁-C₂ alkylamino or C₂-C₄        dialkylamino;    -   W is O;    -   Q is CR^(6a)R^(6b), O, C═N—O—R⁷ or NR⁷; and    -   Y is Z.

Embodiment C1

A compound of Embodiment C wherein

-   -   R¹ is halogen, CN, C₁-C₂ alkyl or C₁-C₂ haloalkyl;    -   R² is H or halogen;    -   R³ is H, C₁-C₂ alkyl or C₁-C₂ haloalkyl;    -   R⁴ is C₁-C₂ alkoxy or C₁-C₂ haloalkoxy;    -   R⁵ is C₁-C₃ alkyl; and    -   Y is Z-1, Z-2, Z-3, Z-4, Z-6, Z-7, Z-8, Z-9, Z-1, Z-12, Z-18 or        Z-24.

Embodiment C2

A compound of Embodiment C1 wherein each R¹⁴ is independently C₁-C₆alkyl, C₃-C₈ cycloalkyl, C₁-C₆ haloalkyl, C₁-C₆ haloalkoxy, or G^(A)each optionally substituted with one or more substituents independentlyselected from the group halogen, cyano, hydroxy, amino, nitro, —CH(═O),—C(═O)OH, —C(═O)NH₂, C(R¹⁵)═N—O—R¹⁶, C(R¹⁵)═N—R¹⁶, C₁-C₆ alkyl, C₃-C₈cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl,C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy and C₃-C₁₀ trialkylsilyl.

Embodiment C3

A compound of Embodiment C2 wherein each G^(A) is independently phenyl,benzyl or 5- or 6-membered heteroaromatic ring, each optionallysubstituted with one or more substituents independently selected fromthe group halogen, —CH(═O), —C(R¹⁵)═N—O—R¹⁶, C(R¹⁵)═N—R¹⁶, C₁-C₆ alkyl,C₃-C₈ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆ alkoxy,C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy and C₃-C₁₀ trialkylsilyl.

Embodiment C4

A compound of Embodiment C3 wherein each G^(A) is independently phenylor 1,2,4-thiadiazole each optionally substituted with one or moresubstituents independently selected from the group halogen, C₁-C₆ alkyl,C₃-C₈ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy andC₃-C₁₀ trialkylsilyl.

Embodiment C5

A compound of Embodiment C wherein Q is CR^(6a)R^(6b).

Embodiment C6

A compound of Embodiment C wherein

-   -   V is NR³.

Embodiment C

A compound of Embodiment C wherein

-   -   V is NR³; and    -   Q is C═N—O—R⁷.

Specific embodiments include compounds of Formula 1 selected from thegroup consisting of:

-   methyl    N-[[2-chloro-5-[1-[[2-(trimethylsilyl)ethoxy]imino]ethyl]phenyl]-methyl]carbamate,-   methyl    N-[[2-chloro-5-[1-[[2-(trimethylsilyl)propoxy]imino]ethyl]phenyl]-methyl]carbamate,-   methyl    2-[4-chloro-3′-(trifluoromethoxy)[1,1′-biphenyl]-3-yl]hydrazinecarboxylate,    methyl    N-[[2-chloro-5-[1-[[(trimethylsilyl)methoxy]imino]ethyl]phenyl]-methyl]carbamate,-   methyl    N-[[2-chloro-5-[1-[[(ethyldimethylsilyl)methoxy]imino]ethyl]phenyl]-methyl]carbamate;-   methyl    N-[[2-chloro-5-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate;-   methyl    N-[[2-chloro-5-[1-(4-methoxyphenyl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate;-   methyl    N-[[5-[1-(4-acetylphenyl)-1H-pyrazol-3-yl]-2-chlorophenyl]methyl]carbamate;-   methyl    N-[[2-chloro-5-[1-[3-(trimethylsilyl)propyl]-1H-pyrazol-3-yl]phenyl]methyl]carbamate;    and-   methyl    N-[[2-chloro-5-[1-[4-methylphenyl)methyl]-1H-pyrazol-3-yl]phenyl]methyl]carbamate.

This invention provides a fungicidal composition comprising a compoundof Formula 1 (including all geometric and stereoisomers, N-oxides, andsalts thereof), and at least one other fungicide. Of note as embodimentsof such compositions are compositions comprising a compoundcorresponding to any of the compound embodiments described above.

This invention provides a fungicidal composition comprising afungicidally effective amount of a compound of Formula 1 (including allgeometric and stereoisomers, N-oxides, and salts thereof), and at leastone additional component selected from the group consisting ofsurfactants, solid diluents and liquid diluents. Of note, as embodimentsof such compositions, are compositions comprising a compoundcorresponding to any of the compound embodiments described above.

This invention provides a method for controlling plant diseases causedby fungal plant pathogens comprising applying to the plant or portionthereof, or to the plant seed, a fungicidally effective amount of acompound of Formula 1 (including all geometric and stereoisomers,N-oxides, and salts thereof). Of note as embodiment of such methods aremethods comprising applying a fungicidally effective amount of acompound corresponding to any of the compound embodiments describeabove. Of particular note are embodiments where the compounds areapplied as compositions of this invention.

One or more of the following methods and variations as described inSchemes 1-21 can be used to prepare the compounds of Formula 1. Thedefinitions of R¹, R², R³, R⁴, R⁵, R^(6a), R^(6b), R^(8a), R^(8b),R^(9a), R^(9b), R^(10a), R^(10b), R^(10c), R¹⁴, G^(A), W, Q, X, Y, p andq in the compounds of Formulae 1-30 below are as defined above in theSummary of the Invention unless otherwise noted. Compounds of Formulae1a-1m are various subsets of Formula 1, and all substituents forFormulae 1a-1m are as defined above for Formula 1 unless otherwisenoted. Formulae 2a, 2b and 2c are subsets of Formula 2, Formula 6a is asubset of Formula 6, Formula 8a is a subset of Formula 8 and Formula 10ais a subset of Formula 10.

As shown in Scheme 1 certain compounds of Formula 1a, (Formula 1 whereinV is NR³ and Y is—C(R⁵)═N—O—(CR^(8a)R^(8b))_(p)—X—(CR^(9a)R^(9b))_(q)—SiR^(10a)R^(10b)R^(10c)),can be prepared by first reacting a compound of Formula 2 withhydroxylamine at temperatures ranging from about 50 to about 100° C. ina lower alkanol solvent such as methanol or ethanol, which canoptionally containing water. The resulting oxime of Formula 3 can thenbe alkylated with a terminal alkyl halide of Formula 4 wherein TA is—(CR^(8a)R^(8b))_(p)—X—(CR^(9a)R^(9b))_(q)—SiR^(10a)R^(10b)R^(10c) andX¹ is a leaving group such as halide (i.e. Cl, Br, I) in a polar aproticsolvent such as N,N-dimethylformamide in the presence of an inorganicbase such as potassium carbonate or sodium hydride at temperaturesranging from about 50 to about 120° C. The method of Scheme 1 isillustrated in Example 2.

Alternatively, compounds of Formula 1a can be prepared by reacting ahydroxylamine derivative of Formula 5 or salt thereof with a compound ofFormula 2 in a lower alkanol solvent at temperatures ranging from about50 to about 100° C. as shown in Scheme 2. For a reference illustratingthis type of reaction see, for example, de Lijser et al., J. OrganicChem. 2004, 69, 3057-3067. The method of Scheme 2 is also illustrated inExample 1.

For a general reference for the synthesis of compounds of Formula 5 seeKikugawa et al., Organic Preparations and Procedures International,1994, 26(1), 111-113.

Compounds of Formula 1b (Formula 1 wherein V is NR³) wherein Y is asubstituted phenyl ring or a 5- or 6-membered heteroaromatic ring can beprepared by the well known Suzuki reaction via Pd-catalyzedcross-coupling of an aromatic iodide or bromide of Formula 6a (Formula6, shown in Scheme 5, wherein X² is Br or I) with a substituted phenylor heteroaromatic boronic acid of Formula 7 as shown in Scheme 3. Fortypical Suzuki reactions conditions see, for example, Suzuki et al.,Chemical Review, 1995, 95, 2457-2483. A wide variety of catalysts areuseful for this type of transformation; particularly useful as acatalyst is tetrakis(triphenylphosphine)palladium(0). Solvents such astetrahydrofuran, acetonitrile, diethyl ether and dioxane are suitable.The boronic acids of Formula 7 are either commercially available or canbe prepared by known methods. Other coupling procedures offer a numberof alternatives for introduction of a substituted phenyl group ontoFormula 1, including coupling methods published by Heck, Stille andKumada. Also see, for example, Zificsak et al., Tetrahedron, 2004, 60,8991-9016. Compounds of Formula 1b wherein Y is a N-linkedheteroaromatic ring can be prepared via a palladium cross-couplingreaction using compounds of Formula 7a. For leading references see, forexample, Buchwald et al., Accounts of Chemical Research, 1998, 31(12),805-818 and Hartwig, Angew. Chem. Int. Ed., 1998, 37, 2046-2067.

As shown in Scheme 4, compounds of Formula 2 can be prepared by reactinga substituted amine of Formula 8 with an acid chloride of Formula 9 inthe presence of a base such as triethylamine or pyridine. The reactioncan be carried out without solvent other than the compounds of Formulae6a, 9 and the base or in an aprotic solvent such as dichloromethane,chloroform, diethyl ether or tetrahydrofuran at temperatures rangingfrom about 0 to about 50° C. For a related reference see European PatentPublication EP 1586552. For a general synthesis of compounds of Formula9, see Advanced Organic Synthesis, 4^(th) Edition, Wiley & Sons 1992,437, and references cited therein. For synthesis of a compound ofFormula 2 wherein Q is NR⁷ and R⁷ is H see World Patent Publication WO2004/037770, and also see Step B of Example 1.

Additionally, compounds of Formula 2a (Formula 2 wherein R⁵ is CH₃) canbe prepared from compounds of Formula 6 by reaction with aceticanhydride in the presence of a palladium catalysis as shown in Scheme 5.For a reference illustrating the method of Scheme 5 see, for example,Cacchi et al., Organic Letters 2003, 5(3), 289-291.

As shown in Scheme 6, compounds of Formula 6 can be prepared from aminesof Formula 10 by a method analogous to Scheme 4. Also, U.S. Pat. No.6,313,071 describes the method of Scheme 6 when Q is CH₂. Additionally,U.S. Pat. No. 6,313,071 describes an alternative method for preparingcertain compounds of Formula 6 when Q is CH₂, involving first preparingan isocyanate from the amine of Formula 10 and then reacting theisocyanate with a compound of Formula R⁴H wherein R⁴ is alkoxy oralkylamino to provide a compound of Formula 6. For synthesis of acompound of Formula 6 wherein Q is NR⁷ and R⁷ is H see Step C of Example1.

Compounds of Formula 8a (Formula 8 wherein Q is CR^(6a)R^(6b)) can beprepared by a simple three-step procedure from amines of Formula 11 asoutlined in Scheme 7. The amines of Formula 11 are known or can beeasily synthesized by general methods known to one skilled in the art.In the first step, an amine of Formula 11 is reacted with aceticanhydride with or without an aprotic solvent such as dichloromethane,chloroform, diethyl ether or tetrahydrofuran at temperatures rangingfrom about 0 to about 100° C., in the presence of a base such astriethylamine or pyridine with or without a nucleophilic catalyst suchas 4-dimethylaminopyridine to provide a compound of Formula 12. Thecompound of Formula 12 can then be reacted according to Friedel-Craftsconditions to provide a compound of Formula 2b (Formula 2 wherein Q isCR^(6a)R^(6b)) which can then be deprotected to yield a compound ofFormula 8a. For typical reactions conditions see, European PatentPublication EP 1586552.

Compounds of Formula 10 are known or can be easily synthesized bygeneral methods known to one skilled in the art. For example, compoundsof Formula 10a (Formula 10 wherein Q is O and R³ is H) can be preparedfrom simple fluorobenzene derivatives of Formula 14 as shown in Scheme8. The reaction of a compound of Formula 14 with a acetohydroxamate ofFormula 15 is typically carried out in a polar aprotic solvent such asN,N-dimethylformamide in the presence of a suitable base such aspotassium tert-butoxide or sodium hydride at temperatures ranging fromabout −10 to 120° C. The resulting compound of Formula 16 can then bedeprotected using a strong acid such as perchloric acid at temperaturesranging from about −10 to about 40° C. to give a compound of Formula 10a(for a relevant reference see, for example, Kikugawa et al., OrganicPreparations and Procedures International 1997, 29(5), 594-600).

Compounds of Formula 1c (Formula 1 wherein V is NR³ and Q is C(═O))wherein Y is a substituted phenyl ring or a 5- or 6-memberedheteroaromatic ring can be prepared according to the method of Scheme 9.In the first step of the method of Scheme 9 a compound of Formula 18 isreacted with a suitable base such as sodium hydride or potassiumtert-butoxide in a solvent such as tetrahydrofuran orN,N-dimethylformamide and then reacted with a compound of Formula 17,which is either commercially available or readily prepared from thecorresponding carboxylic acid by known procedures, at temperaturesranging from about −10 to about 40° C. to yield a compound of Formula6a.

Compounds of Formula 1c can then be prepared by Suzuki reaction couplingprocedures using a substituted phenyl or heteroaromatic boronic acid ofFormula 7 via Pd-catalyzed cross-coupling of the aromatic iodide orbromide compound of Formula 6a (for reaction conditions see, forexample, Suzuki, et al., Chemical Review, 1995, 95, 2457-2483).Compounds of Formula 1c wherein Y is a N-linked heteroaromatic ring canbe prepared via a palladium cross-coupling reaction using compounds ofFormula 7a. For leading references see, for example, Buchwald et al.,Accounts of Chemical Research, 1998, 31(12), 805-818 and Hartwig, Angew.Chem. Int. Ed., 1998, 37, 2046-2067. For a general synthesis ofcompounds of Formulae 17 and 18 see, for example, Advanced OrganicSynthesis, 4^(th) Edition, Wiley & Sons 1992, 417-418, and 437.

Compounds of Formula 1d (Formula 1 wherein Y is wherein is—C(R⁵)═N—O—(CR^(8a)R^(8b))_(p)—X—(CR^(9a)R^(9b))_(q)—SiR^(10a)R^(10b)R^(10c)and R⁵ is CH₃) can be prepared as shown in Scheme 10. The method firstinvolves reacting a compound of Formula 6a with a vinyl ether of Formula19 in the presence of a palladium catalysis according to the generalprocedures reported in the literature (see, for example, Xiao et al., J.Organic Chem. 2006, 71, 7467-7470) to give a compound of Formula 2a. Thecompound of Formula 2a can then be converted to a compound of Formula 1daccording to the method of Scheme 1 or 2.

As shown in Scheme 11, certain compounds of Formula 1e (Formula 1wherein V is NR³ and Y is Z-2) wherein R¹⁴ is H, alkyl or haloalkyl canbe prepared by first reacting a compound of Formula 2c withN,N-dimethylformamide dimethyl acetal (DMF-DMA) at temperatures rangingfrom about 40 to about 100° C. in a lower alkanol solvent such asmethanol or ethanol, which can optionally comprise water, to provide anintermediate compound of Formula 19. In a subsequent step, the compoundof Formula 19 is reacted with hydrazine to provide a compound of Formula1e. One skilled in the art will recognize that there are other methodsfor performing transformations of this type, for example, the methoddescribed by Barrett et al., Bioorganic and Medicinal Chemistry Letters2005, 15, 3540-3546. The method of Scheme 11 is illustrated in Steps Aand B of Example 4.

As shown in Scheme 12, certain compounds of Formula 1f (Formula 1wherein V is NR³ and Y is Z-2) wherein R¹⁴ is H, alkyl or haloalkyl andG^(A) is an optionally substituted phenyl ring, benzyl ring or a 5- or6-membered heteroaromatic can be prepared from a compound of Formula 1eby reaction with a compound of Formula 7^(a′). The reaction isoptionally run in the presence of a catalyst, typically comprisingpalladium or copper. For leading references see Buchwald et al.,Accounts of Chemical Research, 1998, 31(12), 805-818. Alternatively,compounds of Formula 1f can be prepared by reacting a compound ofFormula 1e with a boronic acid of Formula 7 in the presence of asuitable copper salt to provide compounds of Formula 1f. For leadingreferences see Chan et al., in Boronic Acids, 205-240, D. G. Hall, Ed.,Wiley-VCH. Example 5 illustrates the method of Scheme 12 for thepreparation of a compound of Formula 1f from Formula 1e using a boronicacid of Formula 7. Also, Example 5, Example 6, and Step B of Example 8illustrate the method of Scheme 12 using a compound of Formula 7^(a′).

Certain compounds of Formula 1g (Formula 1 wherein V is NR³ and Y isZ-18) can be prepared by reacting a compound of Formula 19 with anamidine of Formula 20 in the presence of a suitable alkoxide base suchas potassium tert-butoxide or alkali hydride base such as sodium hydrideat a temperature ranging from about 50 to about 100° C. in a loweralkanol solvent (e.g., methanol or ethanol) to provide a compound ofFormula 1g.

Compounds of Formula lbh (Formula 1 wherein V is NR³ and Y is Z-11, Z-12or Z-13) wherein R¹⁴ is H can be prepared in three-step synthesisstarting from a compound Formula 6a as outlined in Scheme 14.

In step 1 of Scheme 14, trimethylsilyl substituted alkynes of Formula 20are obtained by contacting a compound of Formula 6a withethynyltrimethylsilane in the presence of a suitable palladium catalyst(such as, for example, tetrakis(triphenylphosphine)palladium ordichlorobis(triphenylphosphine)palladium) and in the presence of asuitable copper catalyst (such, as for example, copper(I) iodide). Inthis method the mole ratio of ethynyltrimethylsilane to the compound ofFormula 6a is typically from about 1.1 to about 5, and the mole ratiosof the palladium catalyst and the copper catalyst to the compound ofFormula 6a are each about 0.005 to about 0.1. The reaction is preferablyrun in the presence of a suitable amine base such as, for example, anamine base comprising triethylamine, N,N-diisopropylethylamine,diethylamine or piperidine. The reaction is preferably conducted in thepresence of a solvent. However, in some cases the reaction can becarried out without solvent other than the compound of Formula 6a, theethynyltrimethylsilane and the amine base. But a preferred procedureinvolves use of a suitable solvent including, for example,tetrahydrofuran, toluene or N,N-dimethylformamide. Further preferred asa solvent is a mixture of the suitable solvent with the amine base. Whenthe solvent comprises the amine base or a combination of the amine baseand the suitable solvent, the amine base is typically in largestoichiometric excess relative to the compound of Formula 6a. For anexample illustrating the method Scheme 14 for the preparation of acompound of Formula 20 see Step C of Example 9.

In step 2 of Scheme 14, removal of the trimethylsilane group to give analkyne of Formula 21 is achieved by treating a compound Formula 20 withan alkali metal hydroxide or carbonate such as potassium hydroxide,sodium hydroxide or potassium carbonate in methanol or ethanol.Typically the mole ratio of the base to the compound of Formula 20 isfrom about 0.001 to about 5. The reaction is preferably conducted in asuitable organic solvent. Typically, the method is most satisfactorilyconducted at a temperature ranging from about 0° C. to the refluxtemperature of the solvent, and most preferably from about 25 to 30° C.Alternatively, other disilylating conditions known in the art can beused, such as treatment with tetrabutylammonium fluoride in solventssuch as tetrahydrofuran and chloroform (optimally comprising water). Foran example illustrating the method of Scheme 14 for the preparation of acompound of Formula 21 see Step D of Example 9.

In step 3 of Scheme 14, compounds of Formula lbh are prepared byreacting alkynes of Formula 21 with a suitable source of azide ions andin the presence of at least one copper(I) salt. Suitable azide sourcesinclude, for example, sodium azide and trimethylsilyl azide. The moleratio of the azide source relative to the compound of Formula 21 istypically from about 1 to about 3. In the present method, suitablecopper(I) salts comprise one or more compounds selected from the groupconsisting of copper(I) iodide, copper(I) bromide and copper(I)chloride. Alternatively, a copper(II) salt can be used in combinationwith a mild reducing agent, for example copper(II) sulfate with sodiumascorbate. The mole ratio of the copper(I) salt to the compound ofFormula 21 is typically from about 0.05 to about 0.2. The reaction istypically run in a solvent such as N,N-dimethylformamide,tetrahydrofuran, methanol, tert-butanol, dimethyl sulfoxide (optionallycomprising water), at temperatures from about 25 to 100° C. The use oflower boiling solvents can in some cases necessitate the need forelevated pressure to facilitate running the reaction at temperatureshigher then the normal boiling point of the solvent. For leadingreferences describing the method of step 3 of Scheme 14 see Jin et al.,European J. Organic Chem. 2004, 3789-3791; Anderson et al., Synlett2005, 2941-2947; and Weinreb et al., Tetrahedron Letters 2006, 47,3035-3038. For an example illustrating the method of Scheme 14 for thepreparation of a compound of Formula lbh see Step E of Example 9.

As depicted in Scheme 15, compounds of the Formula lbh are useful asintermediates for preparing compounds of Formula 1i (Formula 1 wherein Vis NR³ and Y is Z-11, Z-12 or Z-13) wherein R¹⁴ is other than H. Forexample, compounds of Formula 11 wherein R¹⁴ is an optionallysubstituted N-alkyl group can be obtained by treating a compound ofFormula 1h with an alkylating agent, typically in amount ranging fromabout 1 to about 10 molar equivalents relative to the compound ofFormula 1h. The reaction is preferably run in the presence of a basesuch as potassium carbonate, sodium hydride or potassium tert-butoxidetypically in an amount ranging from about 1 to 10 molar equivalents.Optimum results are usually obtained when the reaction is run in a polarsolvent such as N,N-dimethylformamide, tetrahydrofuran, acetone,2-butanone or dimethyl sulfoxide, at temperatures ranging from about 0°C. to 150° C. (depending on the solvent). Typically these reactionconditons provide a mixture of N-alkylated triazole isomers of Formula11, which can be purified by chromatography. For representativeprocedures see Caliendo et al., European Journal of PharmaceuticalSciences, 2002, 16, 15-28; Seto et al., Bioorganic & Medicinal Chemistry2005, 13, 363-386; and Fray et al., J. Medicinal Chemistry 2001, 44,1951-1962. Also, Example 11 illustrates the method of Scheme 15 for thepreparation of a compound of Formula 1h wherein R¹⁴ is 4-methylbenzyl.

Compounds of Formula 1h can also be N-arylated to provide certaincompounds of Formula 1i wherein R¹⁴ is an optionally substitutedN-phenyl ring. This can be accomplished by reacting a compound ofFormula 1h with a phenyl iodide, bromide or chloride in the presence ofiron(III) acetylacetonate (Fe(acac)₃), copper oxide and cesium carbonatein N,N-dimethylformamide at temperatures ranging from about 25 to about150° C. as described by Taillefer et al., Angew. Chem. Int. Ed. 2007,46, 934-936. Typically mixtures of regioisomers of Formula 11 areobtained from these reactions. Purification of the regioisomers isachieved by chromatography. For representative procedures see Beauchardet al., Tetrahedron 2006, 62, 1895-1903. Also Example 10 illustrates themethod of Scheme 15 when R¹⁴ is 4-chlorophenyl.

Certain compounds of Formula 1i wherein R¹⁴ is cyano can be prepared byreacting a compound of Formula 1h with cyanogen bromide in the presenceof a base such a sodium hydride in solvents such as tetrahydrofuran orN,N-dimethylformamide. For representative procedures see Nakajima etal., J. Organic Chem. 1978, 43(13), 2693-2696.

Certain compounds of Formula 1i wherein R¹⁴ is Cl can be prepared byreacting a compound of Formula lbh with sodium hypochlorite in aceticacid using procedures analogous to those described by Canada et al.,Heterocycles 1985, 23(9), 2225-2228.

The formation of compounds of Formula 1i wherein R¹⁴ is OH can beachieved by reacting a compound of Formula 1h with an oxidizing agentsuch as hydrogen peroxide or m-chlorobenzoic acid (MCPBA) usingprocedures analogous to those described by Uhlmann et al., J. OrganicChem., 1997, 62, 9177-9181 and Begtrup et al., Journal of the ChemicalSociety, Perkin Transactions 1, (3) 1995, 243-247, respectively.Additionally, representative procedures illustrating methods forpreparing certain compounds of Formula 1i wherein R¹⁴ is an optionallysubstituted carbonyl group are described in Chemistry of HeterocyclicCompounds 1984, 20, 1392-1393. Representative procedures for theformation of compounds of Formula 1i wherein R¹⁴ is an alkenyl group aredisclosed in Taillefer et al., Chemistry—A European Journal 2006,12(20), 5301-5313.

As shown in Scheme 16, certain compounds of Formula 1j (Formula 1wherein Q is CH₂ and V is NR³) wherein Z is Z-1 or Z-7 substituted withR¹⁴ and R¹⁴ is other than H can be prepared by brominating a compound ofFormula 22 using a brominating agent such as N-bromosuccinimide (NBS) orbromine. Bromination methods of this type are well documented in thechemical literature. For leading references see, for example, Song etal., Synthetic Communications 2007, 37(19), 3311-3317; Andrus et al.,Organic Letters 2007, 9(23), 4865-4868; Organic & Biomolecular Chemistry2007, 5(16), 2555-2559; Piazzi et al., Journal of Medicinal Chemistry2007, 50(17), 4250-4254 and Zhao et al., Journal of Agricultural andFood Chemistry 2007, 55(14), 5697-5700. Also, U.S. Pat. No. 6,313,071provides an example relevant to the bromination method of Scheme 16.Additionally, Step A of Example 15 illustrates the bromination method ofScheme 16.

In the second step, treatment of the benzyl bromide of Formula 23 withpotassium cyanate or sodium cyanate and a compound of Formula R⁴Hwherein R⁴ is an alkoxy or alkylamino group provides compounds ofFormula 1j. The reaction is typically carried out in a solvent such asN,N-dimethylformamide at temperatures ranging from about roomtemperature to 100° C. according to the procedure described in U.S. Pat.No. 6,313,071, also Step B of Example 15 illustrates the method ofScheme 16.

In a subsequent step, compounds of Formula 1j wherein W is O areconverted to the corresponding thioamides wherein W is S using a varietyof standard thiating reagents such as phosphorus pentasulfide or2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide(Lawesson's reagent).

Compounds of Formula 22 wherein Z is Z-1 are either commerciallyavailable or can be prepared by known methods. As illustrated in Scheme17, compounds of Formula 22a (Formula 22 wherein Z is Z-7) can beprepared by treating a compound of Formula 24 with an oxidizing agentsuch as hydrogen peroxide or silver carbonate according to theprocedures taught by Paulvannan et al., Tetrahedron 2000, 56(41),8071-8076 and Buzykin et al., Synthesis 1993, (1), 59-61.

As shown in Scheme 18, a compound of Formula 24 can be prepared byreacting a compound of Formula 25 with methylamine or2,2-diphenylethylamine according to the procedure given in Paulvannan etal., Tetrahedron 2000, 56(41), 8071-8076 and Buzykin et al., Synthesis1993, (1) 59-61.

In the method of Scheme 19, a compound of Formula 25 is prepared byfirst reacting a an aldehyde of Formula 26 with a hydrazine of Formula27 to provide the intermediate compound of Formula 28. For leadingreference teaching this method see Tetrahedron 2000, 56(41), 8071-8076;Lebedev et al., J. Organic Chemistry 2005, 70(2), 596-602 and Halley etal., Synthetic Communications 1997, 27(7), 1199-1207. In a subsequentstep the compound of Formula 28 is chlorinated using a chlorinatingagent such N-chlorosuccinimide (NCS). For references relevant to thistype of chlorination see Paulvannan et al., Tetrahedron 2000, 56(41),8071-8076; Patel et al., Tetrahedron 1996, 52(2), 661-668 and Chen etal., Chemistry Letters 1998 (2), 285-288. Compounds of Formula 26 can beprepared by methods well documented in the chemistry art, and many arecommercially available.

As shown in Scheme 20, certain compounds of Formula 1k (Formula 1wherein Q is C(═O) and V is a direct bond) wherein W is O can beprepared according to the method disclosed in World Patent PublicationWO 99/28305 and by Walker, Chimia 2003, 57(11), 675-679. Reactionconditons for the method of Scheme 20 for the preparation of a compoundof Formula 1k are also illustrated in Step D of Example 12. Compounds ofFormula 1k are useful intermediates for preparing certain compounds ofFormula 1m (Formula 1 wherein Q is C(═N)—OR⁷ and V is a direct bond)wherein W is O. For leading references relevant to this type of reactionsee, for example, World Patent Publication WO 99/28305 and by Walker,Chimia 2003, 57(11), 675-679. Also, the method of Scheme 20 for thepreparation of a compound of Formula 1m is illustrated in Example 13.

Alternatively, a compound of Formula 1m can also be prepared as shown inScheme 21. The method of Scheme 21 is described in World PatentPublication WO 99/28305 and by Walker, Chimia 2003, 57(11), 675-679.

One skilled in the art will recognize that certain compounds of Formula1m wherein R⁴ is an alkoxy group can be converted to the correspondingalkylamino compound by treatment of Formula 1m with an amine of FormulaR⁴NH₂. For this type of transformation, one or more equivalents of theamine (i.e. R⁴NH₂) can be used relative to Formula 1m. Alternatively,one equivalent of the amine and an acid scavenger (e.g., triethylamine)can be used. The reaction can be run with or without solvent, includingusing the amine as the solvent, at temperatures ranging between aboutroom temperature and the normal boiling point of the solvent. It isunderstood by one skilled in the art, that when the amine is used as asolvent it will be in large stoichiometric excess relative to thecompound of Formula 1m (Example 14 illustrates this method).

Additionally, one skilled in the art will recognize that compounds ofFormula 1m wherein W is O can be converted to the correspondingthioamides wherein W is S using a variety of standard thiating reagentssuch as phosphorus pentasulfide or2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide(Lawesson's reagent).

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula 1 may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula 1. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula 1.

One skilled in the art will also recognize that compounds of Formula 1and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Examples are, therefore, to be construedas merely illustrative, and not limiting of the disclosure in any waywhatsoever. Steps in the following Examples illustrate a procedure foreach step in an overall synthetic transformation, and the startingmaterial for each step may not have necessarily been prepared by aparticular preparative run whose procedure is described in otherExamples or Steps. Percentages are by weight except for chromatographicsolvent mixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; “s” means singlet, “d” means doublet, “t” meanstriplet, “m” means multiplet, “dd” means doublet of doublets, and “br s”means broad singlet

Example 1 Preparation of methylN-[[2-chloro-5-[1-[[2-(trimethylsilyl)ethoxy]imino]ethyl]phenyl]-methyl]carbamate

A solution of methyl N-[(5-acetyl-2-chlorophenyl)methyl]acetamide (0.15g, 0.62 mmol) (prepared according the method given in European PatentPublication EP 1586552) and 3-trimethylsilylethylhydroxylaminehydrochloride (0.21 g, 1.2 mmol) in ethanol (20 mL) was heated atrefluxed overnight. The ethanol was then removed under reduced pressure,and the residual oil was purified by medium pressure liquidchromatography (0 to 100% gradient of ethyl acetate in hexanes aseluant) to yield the title compound, a compound of the presentinvention, as a clear oil (0.20 g).

¹H NMR (CDCl₃): δ 7.66 (br s, 1H), 7.51 (m, 1H), 7.34 (d, 1H), 5.21 (brs, 1H), 4.46 (d, 2H), 4.28 (m, 2H), 3.69 (s, 3H), 2.20 (s, 3H), 1.09 (m,2H), 0.06 (s, 9H).

Example 2 Preparation of methylN-[[2-chloro-5-[1-[[2-(trimethylsilyl)propoxy]imino]ethyl]phenyl]-methyl]carbamate

To a solution of methyl N-[(5-acetyl-2-chlorophenyl)methyl]acetamide(0.5 g, 2.1 mmol) (prepared according the method given in EuropeanPatent Publication EP 1586552) in ethanol (10 mL) was added an aqueoussolution hydroxylamine (50% by wt) (0.82 g, 12.4 mmol). The reactionmixture was heated at refluxed overnight, and then concentrated toprovide methylN-[[2-chloro-5-[1-(hydroxyimino)ethyl]phenyl]methyl]carbamate as a whitesolid, which was used without purification. To N,N-dimethylformamide(5.0 mL) was added methylN-[[2-chloro-5-[1-(hydroxyimino)ethyl]phenyl]methyl]carbamate (0.28 g,1.1 mmol), 3-(chloropropyl)trimethylsilane (0.33 g, 2.2 mmol) andpotassium carbonate (0.45 g, 3.3 mmol). This reaction mixture was thenheated at 100° C. overnight, and then concentrated under reducedpressure. The resulting oil was purified by medium pressure liquidchromatography (0 to 100% gradient of ethyl acetate in hexanes aseluant) to yield the title compound, a compound of the presentinvention, as a clear oil. (0.22 g).

¹H NMR (CDCl₃): δ 7.66 (br s, 1H), 7.52 (m, 1H), 7.35 (m, 1H), 5.18 (m,1H), 4.46 (d, 2H), 4.14 (m, 2H), 3.69 (s, 3H), 2.21 (s, 3H), 1.71 (m,2H), 0.54 (m, 2H), 0.01 (m, 9H).

Example 3 Preparation of methyl2-[4-chloro-3′-(trifluoromethoxy)[1,1′-biphenyl]-3-yl]hydrazinecarboxylate Step A: Preparation of 5-bromo-2-chlorophenylhydrazinehydrochloride

A suspension of 5-bromo-2-chloroaniline (23 g, 0.11 mol) in concentratedhydrochloric acid (150 mL) and water (90 mL) was cooled in an ice/saltbath. A solution of sodium nitrite (8 g, 0.11 mol) in water (50 mL) wasadded dropwise to the reaction mixture while maintaining the temperaturebelow 4° C. After stirring for 30 minutes the suspension was transferredvia cannula to a solution of SnCl₂ dihydrate in concentratedhydrochloric acid (170 mL) and cooled to 5° C. The resulting thicksuspension was stirred for 2 h at 5° C. and the solid was isolated viafiltration. The solid was air dried and then further dried by addingchlorobutane (500 mL) and refluxing using a Dean-Stark condenser. Aftercooling, the solid was isolated by filtration to afford the titlecompound as an off-white solid (35.3 g). ¹H NMR (CD₃COCD₃): δ 10.25 (brs, 1H), 8.32 (br s, 2H) 7.38 (d, 1H), 7.30 (d, 1H), 7.16 (dd, 1H).

Step B Preparation of methyl 2-(5-bromo-2-chlorophenyl)hydrazinecarboxylate

To a mixture of 2-(5-bromo-2-chlorophenyl) hydrazine carboxylic acidmethyl ester (i.e. the product of Step A) (2.1 g, 8 mmol) and methylchloroformate (1 mL, 13 mmol) in tetrahydrofuran at 0° C. was addedN,N-diisopropylethylamine (4 mL, 24 mmol). The reaction mixture wasallowed to slowly warm to room temperature and was stirred for threedays. Ethyl acetate and water were added. The layers were separated, andthe aqueous layer was extracted with ethyl acetate. The combined organiclayers were washed with water and a solution of saturated aqueous sodiumchloride and dried. The solvent was removed under reduced pressure toafford the title compound as a pale yellow solid (1.4 g).

¹H NMR (CDCl₃): δ 7.13 (d, 1H), 7.08 (d, 1H), 7.16 (dd, 1H), 6.60 (br s,1H), 6.23 (br s, 1H), 3.29 (s, 3H).

Step C Preparation of methyl2-[4-chloro-3′-(trifluoromethoxy)[1,1′-biphenyl]-3-yl]hydrazinecarboxylate

A mixture of methyl 2-(5-bromo-2-chlorophenyl)hydrazine carboxylate(i.e. the product of Step B) (1.27 g, 4.5 mmol),[3-(trifluoromethoxy)phenyl]boronic acid (1.85 g, 9 mmol), cesiumcarbonate (2.9 g, 9 mmol), tris(dibenzylideneacetone)dipalladium (0.18g, 0.2 mmol) and triphenylphosphine (1.2 g, 4.5 mmol) in toluene (60 mL)and methanol (60 mL) was heated at refluxed for 24 h. After cooling, thereaction mixture was taken up in diethyl ether and washed with water.After drying over sodium sulfate, the solvent was removed under reducedpressure. The residue was purified by flash chromatography using 25%ethyl acetate in hexanes as eluant to afford a solid matieral (1.3 g),which was a mixture of starting material and the title compound.

The solid material was dissolved in toluene (50 mL) and methanol (50mL), and then [3-(trifluoromethoxy)phenyl]boronic acid (0.82 g, 4 mmol),cesium carbonate (2.6 g, 8 mmol), tris(dibenzylideneacetone)dipalladium(0.18 g, 0.2 mmol) and triphenylphosphine (0.52 g, 2 mmol) were added.The reaction mixture was heated at reflux for three days. After cooling,the reaction mixture was taken up in diethyl ether and washed withwater. After drying over sodium sulfate, the solvent was removed underreduced pressure. The residue was purified by flash chromatography (75to 100% gradient of dichloromethane in 1-chlorobutane as eluant) toafford an oily solid (0.67 g). The oily solid was triturated withhexanes to afford the title compound, a compound of the presentinvention, as a white solid (0.475 g) melting at 98-100° C.

¹H NMR (CDCl₃): δ 7.45 (m, 2H), 7.35 (m, 2H), 7.20 (m, 1H), 7.11 (d,1H), 7.02 (dd, 1H), 6.55 (br s, 1H), 6.32 (br s, 1H), 3.78 (s, 3H).

Example 4 Preparation of methylN-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate

Step A: Preparation of methylN-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]methyl]carbamate

A solution of methyl N-[(5-acetyl-2-chlorophenyl)methyl]acetamide (3.5g, 14.5 mmol) (prepared by the method given in European PatentPublication EP 1586552) in N,N-dimethylformamide dimethyl acetal (5.36g, 43.5 mmol) was added to toluene (35 mL). The reaction mixture washeated at reflux overnight and then concentrated under reduced pressure.The resulting residue was dissolved in ethyl acetate and washed withwater (4×). The organic layer was dried over magnesium sulfate, filteredand concentrated to provide the crude product as an oil (4.14 g), whichwas used without further purification.

Step B Preparation of methylN-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate

To a solution of methylN-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]methyl]carbamate(i.e. the product of Step A) (4.14 g, 13.9 mmol) in methanol (80 mL) wasadded hydrazine hydrate (0.771 g, 15.4 mmol). The reaction mixture wasstirred at room temperature for 2 days. The reaction mixture wasfiltered and the solid collected was dried under reduced pressure toprovide the title compound, a compound of the present invention, as asolid (3.26 g).

¹H NMR (DMSO-d₆): δ 12.95 (br s, 1H), 7.80 (d, 2H), 7.70 (m, 1H), 7.44(d, 1H), 6.69 (m, 1H), 4.30 (d, 2H), 3.58 (s, 3H).

Example 5 Preparation of methylN-[[2-chloro-5-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]phenyl]methyl]-carbamate

To a mixture of methylN-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate (i.e. theproduct of Step B, Example 4) (0.2 g, 0.75 mmol),trans-N,N′-dimethylcyclohexane-1,2-diamine (0.043 g, 0.3 mmol),copper(I) iodide (0.03 g, 0.15 mmol) and potassium carbonate (−325 mesh)(0.622 g, 4.5 mmol) in dioxane (4 mL) was added 1-chloro-4-iodobenzene(0.27 g, 1.13 mmol). The reaction mixture heated at reflux overnight andthen concentrated under reduced pressure. The resulting residue waspurified by medium pressure liquid chromatography (0 to 100% gradient ofethyl acetate in hexanes as eluant) to provide the title compound, acompound of the present invention, as a solid (0.156 g) melting at151-153° C.

¹H NMR (CDCl₃): δ 7.92 (m, 2H), 7.77 (m, 1H), 7.71 (m, 2H), 7.43 (m,3H), 6.76 (d, 1H), 5.21 (br s, 1H), 4.52 (d, 2H), 3.70 (s, 3H).

Example 6 Preparation of methylN-[[2-chloro-5-[1-[[3-(trifluoromethoxy)phenyl]methyl]-1H-pyrazol-3-yl]phenyl]methyl]carbamate

A mixture of methylN-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate (i.e. theproduct of Step B, Example 4) (0.2 g, 0.75 mmol),1-(bromomethyl)-3-(trifluoromethoxy)benzene (0.765 g, 3.0 mmol) andpotassium carbonate (−325 mesh, 0.829 g, 6.0 mmol) inN,N-dimethylformamide (4 mL) was heated at 100° C. overnight and thenconcentrated under reduced pressure. The resulting residue was purifiedby medium pressure liquid chromatography (0 to 100% gradient of ethylacetate in hexanes as eluant) to provide the title compound, a compoundof the present invention, as a solid (0.178 g).

¹H NMR (CDCl₃): δ 7.92 (m, 2H), 7.81 (s, 1H), 7.67 (m, 1H), 7.39 (m,3H), 7.15 (t, 2H), 7.08 (s, 1H), 6.59 (d, 1H), 5.36 (s, 2H), 5.20 (br s,1H), 4.49 (d, 2H), 3.69 (s, 3H).

Example 7 Preparation of methylN-[[2-chloro-5-[2-(4-methylphenyl)-4-pyrimidinyl]phenyl]methyl]-carbamate

To mixture of methylN-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]-methyl]carbamate(i.e. the product of Step A, Example 4) (0.43 g, 1.44 mmol),4-methylbenzamidine hydrochloride (0.74 g, 4.33 mmol) and sodium hydride(0.14 g, 5.8 mmol) at 0° C. was slowly added methanol (5 mL). Thereaction mixture was heated at reflux overnight. A solution of saturatedammonium chloride was added to the reaction mixture, and the mixture wasconcentrated under reduced pressure. The resulting residue was dissolvedin ethyl acetate, washed with saturated aqueous sodium carbonate, driedover magnesium sulfate, filtered and concentrated under reducedpressure. The resulting residue was purified by medium pressure liquidchromatography (0 to 100% gradient of ethyl acetate in hexanes aseluant) to provide the title compound, a compound of the presentinvention, as a solid (0.160 g).

¹H NMR (CDCl₃): δ 7.92 (m, 2H), 8.81 (d, 1H), 8.44 (d, 2H), 8.21 (br s,1H), 7.15 (t, 2H), 7.08 (s, 1H), 6.59 (d, 1H), 5.36 (s, 2H), 5.20 (br s,1H), 4.49 (d, 2H), 3.69 (s, 3H).

Example 8 Preparation of methylN-[[2-chloro-5-[1-[3-(1-methylethyl)-1,2,4-thiadiazol-5-yl]-1H-pyrzol-3-yl]phenyl]methyl]carbamate

Step A: Preparation of 5-chloro-3-(1-methylethyl)-1,2,4-thiadiazole

To a mixture of 2-methyl propanimidamide hydrochloride (5.0 g, 40.8mmol), trichloromethanesulfenyl chloride (7.14 g, 38.4 mmol) inmethylene chloride (200 mL) at 0° C. was added dropwise an aqueoussolution of sodium hydroxide (50%, 9.9 mL) over 20 minutes. The reactionmixture was stirred for 2 h at 0° C. and then was allowed to warm toroom temperature, and stirred for an additional 3 h. Ice was added tothe reaction mixture, the mixture was separated, and the aqueous layerwas extracted with methylene chloride (3×25 mL). The combined organicextracts were dried over magnesium sulfate, filtered and concentratedunder reduced pressure. The resulting residue was purified by mediumpressure liquid chromatography (0 to 100% gradient of ethyl acetate inhexanes as eluant) to provide the title compound as a oil (3.8 g).

Step B Preparation of methylN-[[2-chloro-5-[1-[3-(1-methylethyl)-1,2,4-thiadiazol-5-yl]-1H-pyrazol-3-yl]phenyl]methyl]carbamate

A mixture of methylN-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate (i.e. theproduct of Step B, Example 4) (0.02 g, 0.75 mmol),5-chloro-3-(1-methylethyl)-1,2,4-thiadiazole (i.e. the product of StepA) (0.61 g, 3.75 mmol) and potassium carbonate (0.25 g, 1.5 mmol) inN-methyl-2-pyrrolidinone (2.5 mL) was heated in a Biotage Creator XMmicrowave apparatus at 165° C. for 15 minutes. The reaction mixture waspoured into water (60 mL), and the aqueous mixture was extracted withethyl acetate (2×50 mL). The combined organic extracts were washed withwater, dried over magnesium sulfate, filtered and concentrated underreduced pressure. The resulting residue was purified by medium pressureliquid chromatography (0 to 100% gradient of ethyl acetate in hexanes aseluant) to provide the title compound, a compound of the presentinvention, as a solid (0.5 g).

¹H NMR (DMSO-d₆): δ 8.22 (d, 1H), 7.79 (s, 2H), 7.63 (d, 1H), 7.38 (d,1H), 6.74 (d, 1H), 5.42 (br s, 2H), 4.42 (d, 2H), 3.67 (s, 3H), 3.18 (m,1H), 1.37 (d, 6H).

Example 9 Preparation of methylN-[[2-chloro-5-(1H-1,2,3-triazol-5-yl)phenyl]methyl]carbamate Step A:Preparation of 2-(bromomethyl)-1-chloro-4-iodobenzene

To a mixture of 2-chloro-5-iodotoluene (4.07 g, 16.12 mmol),N-bromosuccinimide (3.16 g, 17.73 mmol) in dichloromethane (258 mL) andwater (258 mL) was added 2,2′-azodiisobutyronitrile (0.132 g, 0.81mmol). The reaction mixture was irradiated with a halogen sun lamp (150watt) for 2 h and then cooled to room temperature. The two-phasereaction mixture was separated, and the aqueous layer was extracted withdichloromethane (50 mL). The combined organic layers were washed withwater (2×150 mL), dried over magnesium sulfate, filtered andconcentrated under reduced pressure to provide the title compound as anorange oil (5.20 g).

¹H NMR (CDCl₃): δ 7.76 (d, 1H), 7.58 (d, 1H), 7.11 (d, 1H), 4.49 (s,2H).

Step B Preparation of methyl[(2-chloro-5-iodo-phenyl)methyl]carbamate

To a mixture of potassium carbonate (4.30 g, 53.3 mmol) inN,N-dimethylformamide (47 mL) and methanol (5 mL) at 50° C. was added asolution of 2-(bromomethyl)-1-chloro-4-iodobenzene (i.e. the product ofStep A) (5.20 g, 15.7 mmol) in N,N-dimethylformamide (10 mL). Thereaction mixture was heated at 110° C. for 1 h and then cooled to roomtemperature. The reaction mixture was partitioned between diethyl ether(200 mL) and water (200 mL), the organic layer was separated, washedwith water (3×50 mL), dried over magnesium sulfate, filtered andconcentrated under reduced pressure to provide the title compound as ayellow oil (4.32 g).

¹H NMR (CDCl₃): δ 7.58 (apparent d, 1H), 7.79 (s, 2H), 7.10-7.03 (m,2H), 5.18 (br s, 1H), 4.40 (d, 2H), 3.71 (s, 3H).

Step C Preparation of methylN-[[2-chloro-5-[2-(trimethylsilyl)ethynyl]-phenyl]methyl]carbamate

A mixture methyl[(2-chloro-5-iodo-phenyl)methyl]carbamate (i.e. theproduct of Step B) (3.0 g, 9.2 mmol), ethynyltrimethylsilane (1.94 mL,13.8 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.032 g,0.05 mmol), copper(I) iodide (0.018 g, 0.09 mmol), triphenylphosphine(0.024 g, 0.09 mmol) in tetrahydrofuran (18 mL) and triethylamine (18mL) was stirred at room temperature for 30 minutes. The reaction mixturewas concentrated onto silica gel (7 g) and then purified by mediumpressure liquid chromatography (0 to 25% gradient of ethyl acetate inhexanes as eluant) to provide the title compound as an oil (1.37 g).

¹H NMR (CDCl₃): δ 7.47 (d, 1H), 7.33-7.22 (m, 2H), 5.16 (br s, 1H), 4.41(d, 2H), 3.69 (s, 3H), 0.24 (s, 9H).

Step D Preparation of methylN-[(2-chloro-5-ethynylphenyl)methyl]carbamate

To a solution of methylN-[[2-chloro-5-[2-(trimethylsilyl)ethynyl]phenyl]methyl]-carbamate (i.e.the product of Step C) (1.37 g, 4.6 mmol) in methanol (28 mL) was addedpotassium hydroxide (2.3 mL, 1M in methanol). The reaction mixture wasstirred at room temperature for 18 h, and then concentrated. Theresulting residue was partitioned between ethyl acetate and water, theorganic layer was separated, washed with water, dried over magnesiumsulfate, filtered and concentrated under reduced pressure to provide thetitle compound as a brown oil (0.90 g).

¹H NMR (CDCl₃): δ 7.52 (br s, 1H), 7.38-7.30 (m, 2H), 5.15 (br s, 1H),4.42 (br d, 2H), 3.70 (s, 3H), 3.11 (s, 1H).

Step E Preparation of methylN-[[2-chloro-5-(1H-1,2,3-triazol-5-yl)phenyl]methyl]-carbamate

To a solution of methyl N-[(2-chloro-5-ethynylphenyl)methyl]carbamate(i.e. the product of Step D) (0.43 g, 1.92 mmol) inN,N-dimethylformamide (3.9 mL) and methanol (0.4 mL) was addedtrimethylsilyl azide (0.38 mL, 2.89 mmol) and copper(I) iodide (0.019 g,0.1 mmol). The reaction mixture was heated in a CEM Discover microwaveapparatus at 100° C. for 8 h and then allowed to cool to roomtemperature. The reaction mixture was partitioned between ethyl acetateand aqueous sodium chloride, the layers were separated and the aqueouslayer was extracted with ethyl acetate (2×). The combined organic layerswere washed with water (3×), dried over magnesium sulfate, filtered andconcentrated under reduced pressure to provide the title compound, acompound of the present invention, as a brown solid (0.30 g).

¹H NMR (CDCl₃): δ 7.94 (s, 1H), 7.83 (s, 1H), 7.70 (d, 1H), 7.42 (d,1H), 5.28 (br s, 1H), 4.50 (d, 2H), 3.71 (s, 3H).

Example 10 Preparation of methylN-[[2-chloro-5-[2-(4-chlorophenyl)-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamateand methylN-[[2-chloro-5-[1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate

A mixture of methylN-[[2-chloro-5-(1H-1,2,3-triazol-5-yl)phenyl]methyl]carbamate (i.e. theproduct of Step E, Example 9) (0.53 g, 2.0 mmol), 1-chloro-4-iodobenzene(0.57 g, 2.4 mmol), iron(III) acetylacetonate (0.21 g, 0.6 mmol),copper(II) oxide (0.016 g, 0.2 mmol) and cesium carbonate (1.29 g, 4.0mmol) in N,N-dimethylformamide (4 mL) was heated at 110° C. for 14 h andthen concentrated under reduced pressure. The resulting residue wassuspended in ethanol and then concentrated onto silica gel (2 g). Thesilica gel mixture was purified by flash column chromatography using aSupelco (division of Sigma-Aldrich Co., 595 North Harrison Road,Bellefonte, Pa. 16823, U.S.A.) tube prepacked with 10 g of silica gel(50 μm particle diameter, 70 Å pore size) and 3:1 hexanes-ethyl acetateas eluant to provide methylN-[[2-chloro-5-[2-(4-chlorophenyl)-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate,a compound of the present invention, as a beige solid (0.105 g)

¹H NMR (CDCl₃): δ 8.08 (d, 2H), 8.04 (s, 1H), 7.96 (br s, 1H), 7.75 (dd,1H), 7.48-7.44 (m, 3H), 5.25 (br s, 1H), 4.51 (d, 2H), 3.71 (s, 3H).

Also obtained was methylN-[[2-chloro-5-[1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate,a compound of the present invention, as a brown oil (0.10 g) ¹H NMR(CDCl₃): δ 8.20 (s, 1H), 7.89 (s, 1H), 7.83 (d, 1H), 7.74 (d, 2H), 7.53(d, 2H), 5.24 (br s, 1H), 4.52 (d, 2H), 3.70 (s, 3H).

Example 11 Preparation of methylN-[[2-chloro-5-[2-[(4-methylphenyl)methyl-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamateand methylN-[[2-chloro-5-[1-[(4-methylphenyl)methyl-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate

A mixture of methylN-[[2-chloro-5-(1H-1,2,3-triazol-5-yl)phenyl]methyl]carbamate (i.e. theproduct of Step E, Example 9) (0.24, 0.9 mmol), 4-methylbenzyl bromide(0.17 g, 1.1 mmol) and potassium carbonate (0.25 g, 1.8 mmol) inN,N-dimethylformamide (4.5 mL) was heated at 100° C. for 24 h. Thereaction mixture was allowed to cool and then partitioned betweendiethyl ether (50 mL) and water (30 mL). The organic layer wasseparated, washed with water (3×), dried over magnesium sulfate,filtered and concentrated under reduced pressure. The resulting residuewas dissolved in ethyl acetate and ethanol (2:1 mixture) andconcentrated onto silica gel, and then purified by flash columnchromatography using 5 g of silica gel (0 to 50% gradient of ethylacetate in hexanes as eluant) to provide methylN-[[2-chloro-5-[2-[(4-methylphenyl)methyl-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate,a compound of the present invention, as a colorless oil (0.11 g)

¹H NMR (CDCl₃): δ 7.82 (s, 1H), 7.79 (br s, 1H), 7.61 (d, 1H), 7.38 (d,1H), 7.24 (d, 2H), 7.13 (d, 2H), 5.56 (s, 2H), 5.23 (br s, 1H), 4.48 (d,2H), 3.69 (s, 3H), 2.32 (s, 3H).

Also obtained was methylN-[[2-chloro-5-[1-[(4-methylphenyl)methyl-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate,a compound of the present invention, as a colorless oil (0.10 g)

¹H NMR (CDCl₃): δ 7.77 (s, 1H), 7.72 (d, 1H), 7.65 (s, 1H), 7.39 (d,1H), 7.21 (s, 4H), 5.52 (s, 2H), 5.21 (br s, 3H), 4.41 (d, 2H), 3.67 (2,3H), 2.36 (s, 3H).

Example 12 Preparation of methyl2-methyl-α-oxo-5-[1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]benzeneacetateStep A: Preparation of1-(3-bromo-4-methyl)-3-(dimethylamino)-2-propen-1-one

A solution of 3′-bromo-4′-methylacetophenone (15 g, 70.4 mmol) inN,N-dimethylformamide dimethyl acetal (130 mL, 985 mmol) was heated atreflux overnight. The reaction mixture was cooled to room temperatureand concentrated under reduced pressure. The resulting oil (20.2 g) wascrystallized from hexanes to obtain the title compound as a yellow solid(15.97 g).

¹H NMR (CDCl₃): δ 8.0 (s, 1H), 7.8 (d, 1H), 7.7 (d, 1H), 7.2 (d, 1H),5.6 (d, 1H), 3.1 (br s, 3H), 2.9 (br s, 3H).

Step B Preparation of 3-(3-bromo-4-methylphenyl)-1H-pyrazole

To a solution of 1-(3-bromo-4-methyl)-3-(dimethylamino)-2-propen-1-one(i.e. the product of Step A) (15.97 g, 59.57 mmol) in ethanol (150 mL)was added hydrazine monohydrate (14.4 mL, 299 mmol). The reactionmixture was heated at reflux for 2 h, cooled to room temperature andconcentrated under reduced pressure. The resulting solid was dilutedwith hexanes and filtered to provide the title compound as a white solid(13.95 g).

¹H NMR (CDCl₃): δ 7.9 (s, 1H), 7.62 (d, 1H), 7.6 (d, 1H), 7.2 (d, 1H),6.5 (d, 1H), 2.41 (s, 3H).

Step C Preparation of3-(3-bromo-4-methylphenyl)-1-[3-(trifluoromethyl)phenyl]-1H-pyrazole

To a stirred solution of 3-(3-bromo-4-methylphenyl)-1H-pyrazole (i.e.the product of Step B) (5.0 g, 21.09 mmol) in p-dioxane (19 mL) under anitrogen atmosphere was added 3-iodobenzotrifluoride (5.75 g, 21.11mmol), copper(I) iodide (0.05 g, 0.262 mmol),trans-1,2-diaminocyclohexane (253.5 μL, 2.10 mmol) and potassiumcarbonate (6.1 g, 44.14 mmol). The reaction mixture was heated at 100°C. overnight, cooled to room temperature and diluted with water andethyl acetate. The resulting mixture was separated, and the aqueouslayer was extracted with ethyl acetate (3×). The combined organic layerswere washed with hydrochloric acid (1N), saturated aqueous sodiumchloride, dried over magnesium sulfate, filtered and concentrated underreduced pressure to provide a solid (9 g). Hexanes were added to thesolid, and the mixture was filtered to obtain the title compound as asolid (6.4 g).

¹H NMR (CDCl₃): δ 8.08 (s, 1H), 8.0 (s, 2H), 7.99 (s, 1H), 7.7 (d, 1H),7.6-7.5 (m, 2H), 7.3 (d, 1H), 6.7 (d, 1H), 2.4 (s, 3H).

Step D Preparation of methyl2-methyl-α-oxo-5-[1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]benzeneacetate

To a mixture of magnesium turnings (0.17 g, 6.98 mmol) and1,2-dibromoethane (2 drops) in tetrahydrofuran (0.5 mL) under a nitrogenatmosphere was added dropwise a solution of3-(3-bromo-4-methylphenyl)-1-[3-(trifluoromethyl)phenyl]-1H-pyrazole(i.e. the product of Step C) (2.0 g, 5.25 mmol) in tetrahydrofuran (3.5mL). After about 2% of the total volume of the3-(3-bromo-4-methylphenyl)-1-[3-(trifluoromethyl)phenyl]-1H-pyrazolesolution had been added, the addition was stopped and iodine (catalyticamount) was added to the reaction mixture. The remaining3-(3-bromo-4-methylphenyl)-1-[3-(trifluoromethyl)-phenyl]-1H-pyrazolesolution was then added to the reaction mixture over 1 h while heatingat reflux. Heating was continued for an additional 45 minutes, and thenthe reaction mixture was cooled to room temperature. The reactionmixture was added via an addition funnel to a solution of oxalylchloride (0.508 mL, 5.82 mmol) in tetrahydrofuran (6 mL) at −65° C.Stirring was continued for 2 h at −65° C., and then methanol (1.17 mL)was added to the reaction mixture, and the mixture was allowed to warmto room temperature and stirred for 2 h. The reaction mixture wasdiluted with saturated aqueous ammonium chloride (4 mL) and water (8 mL)and then extracted with ethyl acetate (2×).

The combined organic layers were washed with saturated aqueous sodiumchloride, dried over magnesium sulfate, filtered and concentrated underreduced pressure to give an oil. The oil was purified by medium pressureliquid chromatography (0 to 20% gradient of ethyl acetate in hexanes aseluant) to provide an oil (0.31 g). The oil was crystallized fromhexanes-diethyl ether to provide the title compound, a compound of thepresent invention, as a solid (200 mg).

¹H NMR (CDCl₃): δ 8.2 (s, 1H), 8.1-8.0 (m, 3H), 7.9 (d, 1H), 7.6-7.5 (m,2H), 7.4 (d, 1H), 6.8 (d, 1H), 4.0 (s, 3H), 2.6 (s, 3H).

Example 13 Preparation of methylα-(methoxyimino)-2-methyl-5-[1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]benzeneacetamide

A mixture of methyl2-methyl-α-oxo-5-[1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]benzeneacetate(i.e. the product of Step D, Example 12) (0.184 g, 0.475 mmol) andO-methylhydroxylamine hydrochloride (0.048 g, 0.57 mmol) in methanol (2mL) under a nitrogen atmosphere was heated to reflux overnight. Thereaction mixture was cooled to room temperature, diluted with water anddichloromethane, the layers were separated, and the aqueous layer wasextracted with dichloromethane. The combined organic layers were washedwith saturated aqueous sodium chloride, dried over magnesium sulfate,filtered and concentrated under reduced pressure to give a solid (0.21g). The solid was purified by flash column chromatography using a BondElute® tube (manufactured by Varian) prepacked with 5 g of silica gel(50 μm particle diameter, 70 Å pore size) and 0 to 20% gradient of ethylacetate in hexanes as eluent to provide a solid (180 mg). Hexanes anddiethyl ether were added to the solid, and the mixture was filtered toprovide the title compound, a compound of the present invention, as awhite solid (120 mg).

¹H NMR (CDCl₃): δ 8.0 (s, 1H), 7.99 (d, 1H), 7.8 (d, 1H), 7.63 (s, 1H),7.6-7.5 (m, 2H), 7.3 (d, 1H), 6.7 (d, 1H), 4.07 (s, 3H), 3.89 (s, 3H),2.23 (s, 3H).

Example 14 Preparation ofα-(methoxyimino)-N,2-dimethyl-5-[1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]benzeneacetamide

To a solution of methylα-(methoxyimino)-2-methyl-5-[1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]benzeneacetamide(i.e. the product of Example 13) (0.062 g, 0.149 mmol) intetrahydrofuran (2 mL) under a nitrogen atmosphere was added methylamine(33% by weight in ethanol). The reaction mixture was stirred overnightat room temperature and then concentrated under reduced pressure toleave a solid. Hexanes and diethyl ether were added to the solid, andthe mixture was filtered to obtain the tile compound, a compound of thepresent invention, as a white solid (56 mg).

¹H NMR (CDCl₃): δ 8.0 (s, 1H), 7.99 (d, 1H), 7.9 (d, 1H), 7.8 (d, 1H),7.63 (s, 1H), 7.6-7.5 (m, 2H), 7.3 (d, 1H), 7.3 (d, 1H), 6.7 (d, 1H),3.89 (s, 3H), 2.9 (d, 3H), 2.2 (s, 3H).

Example 15 Preparation of methylN-[[2-chloro-5-[3-(4-chlorophenyl)-1H-pyrazol-1-yl]phenyl]methyl]-carbamateStep A: 1-(3-methyl-4-chlorophenyl)-3-(3-chlorophenyl)-1H-pyrazole

A mixture of 3-(3-chlorophenyl)-1H-pyrazole (5.3 g, 29.8 mmol) (preparedaccording to the method given in European Patent Publication EP 538156),salicylaldoxime (0.58 g, 4.25 mmol), 5-bromo-2-chlorotoluene (2.8 g,21.3 mmol), copper oxide (0.15 g, 1.06 mmol) and cesium carbonate (11.8g, 36.2 mmol) in 20 mL of N,N-dimethylformamide was heated at 140° C.overnight and then allowed to cool to room temperature. The resultingsuspension was filtered and the filtrate was concentrated under reducepressure. The resulting residue was purified by medium pressure liquidchromatography (2 to 10% gradient of ethyl acetate in hexanes as eluant)to give the title compound as a white solid (1.4 g).

¹H NMR (CDCl₃): δ 7.92-7.30 (m, 8H), 6.78 (s, 1H), 2.46 (s, 3H).

Step B Preparation of1-(3-bromomethyl-4-chlorophenyl)-3-(3-chlorophenyl)-1H-pyrazole

A mixture of 1-(3-methyl-4-chlorophenyl)-3-(3-chlorophenyl)-1H-pyrazole(i.e. the product of Step A) (1.7 g, 5.61 mmol), N-bromosuccinimide (1.1g, 6.17 mmol) and benzoyl peroxide (30 mg, 0.12 mmol) in 100 mL ofcarbon tetrachloride was irradiated with a sun lamp for 4 hours. Thereaction mixture was concentrated under reduced pressure and the residuewas purified by medium pressure liquid chromatography (10 to 20%gradient of ethyl acetate in hexanes as eluant) to give the titlecompound as a white solid (0.37 g).

¹H NMR (CDCl₃): δ 7.98-7.30 (m, 8H), 6.79 (s, 1H), 4.65 (s, 2H).

Step C Preparation of methylN-[[2-chloro-5-[3-(4-chlorophenyl)-1H-pyrazol-1-yl]phenyl]methyl]carbamate

A mixture of1-(3-bromomethyl-4-chlorophenyl)-3-(3-chlorophenyl)-1H-pyrazole (i.e.the product of Step B) (0.37 g, 0.97 mmol) and potassium cyanate (0.16g, 1.94 mmol) in 3 mL of methanol and 6 mL of N,N-dimethylformamide washeated at 100° C. for 4 hours.

After cooling, the solvent was then removed under reduced pressure andthe residue was purified by medium pressure liquid chromatography (20 to40% gradient of ethyl acetate in hexanes as eluant) to afford the titlecompound, a compound of the present invention, as a tan solid (0.24 g)melting at 127-130° C.

¹H NMR (CDCl₃): δ 7.98-7.30 (m, 8H), 6.78 (s, 1H), 5.25 (m, 1H), 4.53(d, 2H), 3.72 (s, 3H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 10 can be prepared. Thefollowing abbreviations are used in the Tables which follow: i meansiso, c means cyclo, n means normal, s means secondary, t means tertiary,Ac means acetyl, Me means methyl, Et means ethyl, Pr means propyl, OMemeans methoxy, CN means cyano, and Ph means phenyl. Substituents onbenzyl are attached to the phenyl ring of the benzyl, and locant numbersfor the substituents are relative to the phenyl position bonded to themethylene component of benzyl. In Tables 1-3 the left end of themoieties listed for V¹ are bonded to O and the right end is bonded to Siin the depicted molecular structures. In Tables 1-3, Va through Vh havethe following meanings as defined below in Exhibit 4.

Exhibit 4

TABLE 1

R¹ V¹ R^(10a) R^(10b) R^(10c) Cl —CH₂— Me Me Me Cl —CH₂CH₂— Me Me Me Cl—CH₂CH₂CH₂— Me Me Me Cl —CH₂CH₂CH₂CH₂— Me Me Me Cl —CH₂OCH₂CH₂— Me Me MeCl —CH₂CH₂OCH₂— Me Me Me Cl —CH₂C(═O)CH₂CH₂— Me Me Me Cl—CH₂CH₂C(═O)CH₂— Me Me Me Cl —CH₂C(═S)CH₂CH₂— Me Me Me Cl—CH₂CH₂C(═S)CH₂— Me Me Me Cl —CH₂C(═O)CH₂— Me Me Me Cl —CH₂C(═S)CH₂— MeMe Me Cl —CH(Me)— Me Me Me Cl —CH(OMe)— Me Me Me Cl —CH(Me)CH₂— Me Me MeCl —CH₂CH(Me)— Me Me Me Cl —CH₂CH(OMe)— Me Me Me Cl —CH(Me)CH₂CH₂— Me MeMe Cl —CH₂CH(Me)CH₂— Me Me Me Cl —CH₂CH₂CH(Me)— Me Me Me Cl —CH(Et)— MeMe Me Cl —CH(Et)CH₂— Me Me Me Cl —CH₂CH(Et)— Me Me Me Cl —CH(Et)CH₂CH₂—Me Me Me Cl —CH₂CH(Et)CH₂— Me Me Me Cl —CH₂CH₂CH(Et)— Me Me Me Cl—CH(OCF₃)— Me Me Me Cl —CH(CF₃)— Me Me Me Cl —CH₂CF₂CH₂— Me Me Me Cl—CH₂CHFCH₂— Me Me Me Cl —CH₂CF₂— Me Me Me Cl —CH₂CHF— Me Me Me Cl—CH(CN)— Me Me Me Cl V^(a) Me Me Me Cl V^(b) Me Me Me Cl V^(c) Me Me MeCl V^(d) Me Me Me Cl V^(e) Me Me Me Cl V^(f) Me Me Me Cl V^(g) Me Me MeCl V^(h) Me Me Me Cl —CH₂OC(═O)CH₂— Me Me Me Cl —CH₂C(═O)CH₂— Me Me MeCl —CH₂C(═O)— Me Me Me Cl —CH₂— Me Me Et Cl —CH₂CH₂— Me Me Et Cl—CH₂CH₂CH₂— Me Me Et Cl —CH₂CH₂CH₂CH₂— Me Me Et Cl —CH₂OCH₂CH₂— Me Me EtCl —CH₂CH₂OCH₂— Me Me Et Cl —CH₂C(═O)CH₂CH₂— Me Me Et Cl—CH₂CH₂C(═O)CH₂— Me Me Et Cl —CH₂C(═S)CH₂CH₂— Me Me Et Cl—CH₂CH₂C(═S)CH₂— Me Me Et Cl —CH₂C(═O)CH₂— Me Me Et Cl —CH₂C(═S)CH₂— MeMe Et Cl —CH(Me)— Me Me Et Cl —CH(OMe)— Me Me Et Cl —CH(Me)CH₂— Me Me EtCl —CH₂CH(Me)— Me Me Et Cl —CH₂CH(OMe)— Me Me Et Cl —CH(Me)CH₂CH₂— Me MeEt Cl —CH₂CH(Me)CH₂— Me Me Et Cl —CH₂CH₂CH(Me)— Me Me Et Cl —CH(Et)— MeMe Et Cl —CH(Et)CH₂— Me Me Et Cl —CH₂CH(Et)— Me Me Et Cl —CH(Et)CH₂CH₂—Me Me Et Cl —CH₂CH(Et)CH₂— Me Me Et Cl —CH₂CH₂CH(Et)— Me Me Et Cl—CH(OCF₃)— Me Me Et Cl —CH(CF₃)— Me Me Et Cl —CH₂CF₂CH₂— Me Me Et Cl—CH₂CHFCH₂— Me Me Et Cl —CH₂CF₂— Me Me Et Cl —CH₂CHF— Me Me Et Cl—CH(CN)— Me Me Et Cl V^(a) Me Me Et Cl V^(b) Me Me Et Cl V^(c) Me Me EtCl V^(d) Me Me Et Cl V^(e) Me Me Et Cl V^(f) Me Me Et Cl V^(g) Me Me EtCl V^(h) Me Me Et Cl —CH₂OC(═O)CH₂— Me Me Et Cl —CH₂C(═O)CH₂— Me Me EtCl —CH₂C(═O)— Me Me Et Cl —CH₂— Me Et Et Cl —CH₂CH₂— Me Et Et Cl—CH₂CH₂CH₂— Me Et Et Cl —CH₂CH₂CH₂CH₂— Me Et Et Cl —CH₂OCH₂CH₂— Me Et EtCl —CH₂CH₂OCH₂— Me Et Et Cl —CH₂C(═O)CH₂CH₂— Me Et Et Cl—CH₂CH₂C(═O)CH₂— Me Et Et Cl —CH₂C(═S)CH₂CH₂— Me Et Et Cl—CH₂CH₂C(═S)CH₂— Me Et Et Cl —CH₂C(═O)CH₂— Me Et Et Cl —CH₂C(═S)CH₂— MeEt Et Cl —CH(Me)— Me Et Et Cl —CH(OMe)— Me Et Et Cl —CH(Me)CH₂— Me Et EtCl —CH₂CH(Me)— Me Et Et Cl —CH₂CH(OMe)— Me Et Et Cl —CH(Me)CH₂CH₂— Me EtEt Cl —CH₂CH(Me)CH₂— Me Et Et Cl —CH₂CH₂CH(Me)— Me Et Et Cl —CH(Et)— MeEt Et Cl —CH(Et)CH₂— Me Et Et Cl —CH₂CH(Et)— Me Et Et Cl —CH(Et)CH₂CH₂—Me Et Et Cl —CH₂CH(Et)CH₂— Me Et Et Cl —CH₂CH₂CH(Et)— Me Et Et Cl—CH(OCF₃)— Me Et Et Cl —CH(CF₃)— Me Et Et Cl —CH₂CF₂CH₂— Me Et Et Cl—CH₂CHFCH₂— Me Et Et Cl —CH₂CF₂— Me Et Et Cl —CH₂CHF— Me Et Et Cl—CH(CN)— Me Et Et Cl V^(a) Me Et Et Cl V^(b) Me Et Et Cl V^(c) Me Et EtCl V^(d) Me Et Et Cl V^(e) Me Et Et Cl V^(f) Me Et Et Cl V^(g) Me Et EtCl V^(h) Me Et Et Cl —CH₂OC(═O)CH₂— Me Et Et Cl —CH₂C(═O)CH₂— Me Et EtCl —CH₂C(═O)— Me Et Et Cl —CH₂— Et Et Et Cl —CH₂CH₂— Et Et Et Cl—CH₂CH₂CH₂— Et Et Et Cl —CH₂CH₂CH₂CH₂— Et Et Et Cl —CH₂OCH₂CH₂— Et Et EtCl —CH₂CH₂OCH₂— Et Et Et Cl —CH₂C(═O)CH₂CH₂— Et Et Et Cl—CH₂CH₂C(═O)CH₂— Et Et Et Cl —CH₂C(═S)CH₂CH₂— Et Et Et Cl—CH₂CH₂C(═S)CH₂— Et Et Et Cl —CH₂C(═O)CH₂— Et Et Et Cl —CH₂C(═S)CH₂— EtEt Et Cl —CH(Me)— Et Et Et Cl —CH(OMe)— Et Et Et Cl —CH(Me)CH₂— Et Et EtCl —CH₂CH(Me)— Et Et Et Cl —CH₂CH(OMe)— Et Et Et Cl —CH(Me)CH₂CH₂— Et EtEt Cl —CH₂CH(Me)CH₂— Et Et Et Cl —CH₂CH₂CH(Me)— Et Et Et Cl —CH(Et)— EtEt Et Cl —CH(Et)CH₂— Et Et Et Cl —CH₂CH(Et)— Et Et Et Cl —CH(Et)CH₂CH₂—Et Et Et Cl —CH₂CH(Et)CH₂— Et Et Et Cl —CH₂CH₂CH(Et)— Et Et Et Cl—CH(OCF₃)— Et Et Et Cl —CH(CF₃)— Et Et Et Cl —CH₂CF₂CH₂— Et Et Et Cl—CH₂CHFCH₂— Et Et Et Cl —CH₂CF₂— Et Et Et Cl —CH₂CHF— Et Et Et Cl—CH(CN)— Et Et Et Cl V^(a) Et Et Et Cl V^(b) Et Et Et Cl V^(c) Et Et EtCl V^(d) Et Et Et Cl V^(e) Et Et Et Cl V^(f) Et Et Et Cl V^(g) Et Et EtCl V^(h) Et Et Et Cl —CH₂OC(═O)CH₂— Et Et Et Cl —CH₂C(═O)CH₂— Et Et EtCl —CH₂C(═O)— Et Et Et Cl —CH₂— Me Me i-Pr Cl —CH₂CH₂— Me Me i-Pr Cl—CH₂CH₂CH₂— Me Me i-Pr Cl —CH₂CH₂CH₂CH₂— Me Me i-Pr Cl —CH₂OCH₂CH₂— MeMe i-Pr Cl —CH₂CH₂OCH₂— Me Me i-Pr Cl —CH₂C(═O)CH₂CH₂— Me Me i-Pr Cl—CH₂CH₂C(═O)CH₂— Me Me i-Pr Cl —CH₂C(═S)CH₂CH₂— Me Me i-Pr Cl—CH₂CH₂C(═S)CH₂— Me Me i-Pr Cl —CH₂C(═O)CH₂— Me Me i-Pr Cl —CH₂C(═S)CH₂—Me Me i-Pr Cl —CH(Me)— Me Me i-Pr Cl —CH(OMe)— Me Me i-Pr Cl —CH(Me)CH₂—Me Me i-Pr Cl —CH₂CH(Me)— Me Me i-Pr Cl —CH₂CH(OMe)— Me Me i-Pr Cl—CH(Me)CH₂CH₂— Me Me i-Pr Cl —CH₂CH(Me)CH₂— Me Me i-Pr Cl —CH₂CH₂CH(Me)—Me Me i-Pr Cl —CH(Et)— Me Me i-Pr Cl —CH(Et)CH₂— Me Me i-Pr Cl—CH₂CH(Et)— Me Me i-Pr Cl —CH(Et)CH₂CH₂— Me Me i-Pr Cl —CH₂CH(Et)CH₂— MeMe i-Pr Cl —CH₂CH₂CH(Et)— Me Me i-Pr Cl —CH(OCF₃)— Me Me i-Pr Cl—CH(CF₃)— Me Me i-Pr Cl —CH₂CF₂CH₂— Me Me i-Pr Cl —CH₂CHFCH₂— Me Me i-PrCl —CH₂CF₂— Me Me i-Pr Cl —CH₂CHF— Me Me i-Pr Cl —CH(CN)— Me Me i-Pr ClV^(a) Me Me i-Pr Cl V^(b) Me Me i-Pr Cl V^(c) Me Me i-Pr Cl V^(d) Me Mei-Pr Cl V^(e) Me Me i-Pr Cl V^(f) Me Me i-Pr Cl V^(g) Me Me i-Pr ClV^(h) Me Me i-Pr Cl —CH₂OC(═O)CH₂— Me Me i-Pr Cl —CH₂C(═O)CH₂— Me Mei-Pr Cl —CH₂C(═O)— Me Me i-Pr Cl —CH₂— Me Et i-Pr Cl —CH₂CH₂— Me Et i-PrCl —CH₂CH₂CH₂— Me Et i-Pr Cl —CH₂CH₂CH₂CH₂— Me Et i-Pr Cl —CH₂OCH₂CH₂—Me Et i-Pr Cl —CH₂CH₂OCH₂— Me Et i-Pr Cl —CH₂C(═O)CH₂CH₂— Me Et i-Pr Cl—CH₂CH₂C(═O)CH₂— Me Et i-Pr Cl —CH₂C(═S)CH₂CH₂— Me Et i-Pr Cl—CH₂CH₂C(═S)CH₂— Me Et i-Pr Cl —CH₂C(═O)CH₂— Me Et i-Pr Cl —CH₂C(═S)CH₂—Me Et i-Pr Cl —CH(Me)— Me Et i-Pr Cl —CH(OMe)— Me Et i-Pr Cl —CH(Me)CH₂—Me Et i-Pr Cl —CH₂CH(Me)— Me Et i-Pr Cl —CH₂CH(OMe)— Me Et i-Pr Cl—CH(Me)CH₂CH₂— Me Et i-Pr Cl —CH₂CH(Me)CH₂— Me Et i-Pr Cl —CH₂CH₂CH(Me)—Me Et i-Pr Cl —CH(Et)— Me Et i-Pr Cl —CH(Et)CH₂— Me Et i-Pr Cl—CH₂CH(Et)— Me Et i-Pr Cl —CH(Et)CH₂CH₂— Me Et i-Pr Cl —CH₂CH(Et)CH₂— MeEt i-Pr Cl —CH₂CH₂CH(Et)— Me Et i-Pr Cl —CH(OCF₃)— Me Et i-Pr Cl—CH(CF₃)— Me Et i-Pr Cl —CH₂CF₂CH₂— Me Et i-Pr Cl —CH₂CHFCH₂— Me 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4-Cl—Ph Cl —CH(Et)CH₂CH₂— Me Me 4-Cl—PhCl —CH₂CH(Et)CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂CH(Et)— Me Me 4-Cl—Ph Cl—CH(OCF₃)— Me Me 4-Cl—Ph Cl —CH(CF₃)— Me Me 4-Cl—Ph Cl —CH₂CF₂CH₂— Me Me4-Cl—Ph Cl —CH₂CHFCH₂— Me Me 4-Cl—Ph Cl —CH₂CF₂— Me Me 4-Cl—Ph Cl—CH₂CHF— Me Me 4-Cl—Ph Cl —CH(CN)— Me Me 4-Cl—Ph Cl V^(a) Me Me 4-Cl—PhCl V^(b) Me Me 4-Cl—Ph Cl V^(c) Me Me 4-Cl—Ph Cl V^(d) Me Me 4-Cl—Ph ClV^(e) Me Me 4-Cl—Ph Cl V^(f) Me Me 4-Cl—Ph Cl V^(g) Me Me 4-Cl—Ph ClV^(h) Me Me 4-Cl—Ph Cl —CH₂OC(═O)CH₂— Me Me 4-Cl—Ph Cl —CH₂C(═O)CH₂— MeMe 4-Cl—Ph Cl —CH₂C(═O)— Me Me 4-Cl—Ph Cl —CH₂— Me Me 3-Cl—Ph Cl—CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂CH₂CH₂— MeMe 3-Cl—Ph Cl —CH₂OCH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂OCH₂— Me Me 3-Cl—PhCl —CH₂C(═O)CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂C(═O)CH₂— Me Me 3-Cl—Ph Cl—CH₂C(═S)CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂C(═S)CH₂— Me Me 3-Cl—Ph Cl—CH₂C(═O)CH₂— Me Me 3-Cl—Ph Cl —CH₂C(═S)CH₂— Me Me 3-Cl—Ph Cl —CH(Me)—Me Me 3-Cl—Ph Cl —CH(OMe)— Me Me 3-Cl—Ph Cl —CH(Me)CH₂— Me Me 3-Cl—Ph Cl—CH₂CH(Me)— Me Me 3-Cl—Ph Cl —CH₂CH(OMe)— Me Me 3-Cl—Ph Cl—CH(Me)CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH(Me)CH₂— Me Me 3-Cl—Ph Cl—CH₂CH₂CH(Me)— Me Me 3-Cl—Ph Cl —CH(Et)— Me Me 3-Cl—Ph Cl —CH(Et)CH₂— MeMe 3-Cl—Ph Cl —CH₂CH(Et)— Me Me 3-Cl—Ph Cl —CH(Et)CH₂CH₂— Me Me 3-Cl—PhCl —CH₂CH(Et)CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂CH(Et)— Me Me 3-Cl—Ph Cl—CH(OCF₃)— Me Me 3-Cl—Ph Cl —CH(CF₃)— Me Me 3-Cl—Ph Cl —CH₂CF₂CH₂— Me Me3-Cl—Ph Cl —CH₂CHFCH₂— Me Me 3-Cl—Ph Cl —CH₂CF₂— Me Me 3-Cl—Ph Cl—CH₂CHF— Me Me 3-Cl—Ph Cl —CH(CN)— Me Me 3-Cl—Ph Cl V^(a) Me Me 3-Cl—PhCl V^(b) Me Me 3-Cl—Ph Cl V^(c) Me Me 3-Cl—Ph Cl V^(d) Me Me 3-Cl—Ph ClV^(e) Me Me 3-Cl—Ph Cl V^(f) Me Me 3-Cl—Ph Cl V^(g) Me Me 3-Cl—Ph ClV^(h) Me Me 3-Cl—Ph Cl —CH₂OC(═O)CH₂— Me Me 3-Cl—Ph Cl —CH₂C(═O)CH₂— MeMe 3-Cl—Ph Cl —CH₂C(═O)— Me Me 3-Cl—Ph Cl —CH₂— Me Me 2-Cl—Ph Cl—CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂CH₂CH₂— MeMe 2-Cl—Ph Cl —CH₂OCH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂OCH₂— Me Me 2-Cl—PhCl —CH₂C(═O)CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂C(═O)CH₂— Me Me 2-Cl—Ph Cl—CH₂C(═S)CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂C(═S)CH₂— Me Me 2-Cl—Ph Cl—CH₂C(═O)CH₂— Me Me 2-Cl—Ph Cl —CH₂C(═S)CH₂— Me Me 2-Cl—Ph Cl —CH(Me)—Me Me 2-Cl—Ph Cl —CH(OMe)— Me Me 2-Cl—Ph Cl —CH(Me)CH₂— Me Me 2-Cl—Ph Cl—CH₂CH(Me)— Me Me 2-Cl—Ph Cl —CH₂CH(OMe)— Me Me 2-Cl—Ph Cl—CH(Me)CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH(Me)CH₂— Me Me 2-Cl—Ph Cl—CH₂CH₂CH(Me)— Me Me 2-Cl—Ph Cl —CH(Et)— Me Me 2-Cl—Ph Cl —CH(Et)CH₂— MeMe 2-Cl—Ph Cl —CH₂CH(Et)— Me Me 2-Cl—Ph Cl —CH(Et)CH₂CH₂— Me Me 2-Cl—PhCl —CH₂CH(Et)CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂CH(Et)— Me Me 2-Cl—Ph Cl—CH(OCF₃)— Me Me 2-Cl—Ph Cl —CH(CF₃)— Me Me 2-Cl—Ph Cl —CH₂CF₂CH₂— Me Me2-Cl—Ph Cl —CH₂CHFCH₂— Me Me 2-Cl—Ph Cl —CH₂CF₂— Me Me 2-Cl—Ph Cl—CH₂CHF— Me Me 2-Cl—Ph Cl —CH(CN)— Me Me 2-Cl—Ph Cl V^(a) Me Me 2-Cl—PhCl V^(b) Me Me 2-Cl—Ph Cl V^(c) Me Me 2-Cl—Ph Cl V^(d) Me Me 2-Cl—Ph ClV^(e) Me Me 2-Cl—Ph Cl V^(f) Me Me 2-Cl—Ph Cl V^(g) Me Me 2-Cl—Ph ClV^(h) Me Me 2-Cl—Ph Cl —CH₂OC(═O)CH₂— Me Me 2-Cl—Ph Cl —CH₂C(═O)CH₂— MeMe 2-Cl—Ph 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i-Pr Me —CH(CN)— Me Me i-Pr MeV^(a) Me Me i-Pr Me V^(b) Me Me i-Pr Me V^(c) Me Me i-Pr Me V^(d) Me Mei-Pr Me V^(e) Me Me i-Pr Me V^(f) Me Me i-Pr Me V^(g) Me Me i-Pr MeV^(h) Me Me i-Pr Me —CH₂OC(═O)CH₂— Me Me i-Pr Me —CH₂C(═O)CH₂— Me Mei-Pr Me —CH₂C(═O)— Me Me i-Pr Me —CH₂— Me Me Ph Me —CH₂CH₂— Me Me Ph Me—CH₂CH₂CH₂— Me Me Ph Me —CH₂CH₂CH₂CH₂— Me Me Ph Me —CH₂OCH₂CH₂— Me Me PhMe —CH₂CH₂OCH₂— Me Me Ph Me —CH₂C(═O)CH₂CH₂— Me Me Ph Me—CH₂CH₂C(═O)CH₂— Me Me Ph Me —CH₂C(═S)CH₂CH₂— Me Me Ph Me—CH₂CH₂C(═S)CH₂— Me Me Ph Me —CH₂C(═O)CH₂— Me Me Ph Me —CH₂C(═S)CH₂— MeMe Ph Me —CH(Me)— Me Me Ph Me —CH(OMe)— Me Me Ph Me —CH(Me)CH₂— Me Me PhMe —CH₂CH(Me)— Me Me Ph Me —CH₂CH(OMe)— Me Me Ph Me —CH(Me)CH₂CH₂— Me MePh Me —CH₂CH(Me)CH₂— Me Me Ph Me —CH₂CH₂CH(Me)— Me Me Ph Me —CH(Et)— MeMe Ph Me —CH(Et)CH₂— Me Me Ph Me —CH₂CH(Et)— Me Me Ph Me —CH(Et)CH₂CH₂—Me Me Ph Me —CH₂CH(Et)CH₂— Me Me Ph Me —CH₂CH₂CH(Et)— Me Me Ph Me—CH(OCF₃)— Me Me Ph Me —CH(CF₃)— Me Me Ph Me —CH₂CF₂CH₂— Me Me Ph Me—CH₂CHFCH₂— Me Me Ph Me —CH₂CF₂— Me Me Ph Me —CH₂CHF— Me Me Ph Me—CH(CN)— Me Me Ph Me V^(a) Me Me Ph Me V^(b) Me Me Ph Me V^(c) Me Me PhMe V^(d) Me Me Ph Me V^(e) Me Me Ph Me V^(f) Me Me Ph Me V^(g) Me Me PhMe V^(h) Me Me Ph Me —CH₂OC(═O)CH₂— Me Me Ph Me —CH₂C(═O)CH₂— Me Me PhMe —CH₂C(═O)— Me Me Ph Me —CH₂— Me Me 3-Cl—Ph Me —CH₂CH₂— Me Me 3-Cl—PhMe —CH₂CH₂CH₂— Me Me 3-Cl—Ph Me —CH₂CH₂CH₂CH₂— Me Me 3-Cl—Ph Me—CH₂OCH₂CH₂— Me Me 3-Cl—Ph Me —CH₂CH₂OCH₂— Me Me 3-Cl—Ph Me—CH₂C(═O)CH₂CH₂— Me Me 3-Cl—Ph Me —CH₂CH₂C(═O)CH₂— Me Me 3-Cl—Ph Me—CH₂C(═S)CH₂CH₂— Me Me 3-Cl—Ph Me —CH₂CH₂C(═S)CH₂— Me Me 3-Cl—Ph Me—CH₂C(═O)CH₂— Me Me 3-Cl—Ph Me —CH₂C(═S)CH₂— Me Me 3-Cl—Ph Me —CH(Me)—Me Me 3-Cl—Ph Me —CH(OMe)— Me Me 3-Cl—Ph Me —CH(Me)CH₂— Me Me 3-Cl—Ph Me—CH₂CH(Me)— Me Me 3-Cl—Ph Me —CH₂CH(OMe)— Me Me 3-Cl—Ph Me—CH(Me)CH₂CH₂— Me Me 3-Cl—Ph Me —CH₂CH(Me)CH₂— Me Me 3-Cl—Ph Me—CH₂CH₂CH(Me)— Me Me 3-Cl—Ph Me —CH(Et)— Me Me 3-Cl—Ph Me —CH(Et)CH₂— MeMe 3-Cl—Ph Me —CH₂CH(Et)— Me Me 3-Cl—Ph Me —CH(Et)CH₂CH₂— Me Me 3-Cl—PhMe —CH₂CH(Et)CH₂— Me Me 3-Cl—Ph Me —CH₂CH₂CH(Et)— Me Me 3-Cl—Ph Me—CH(OCF₃)— Me Me 3-Cl—Ph Me —CH(CF₃)— Me Me 3-Cl—Ph Me —CH₂CF₂CH₂— Me Me3-Cl—Ph Me —CH₂CHFCH₂— Me Me 3-Cl—Ph Me —CH₂CF₂— Me Me 3-Cl—Ph Me—CH₂CHF— Me Me 3-Cl—Ph Me —CH(CN)— Me Me 3-Cl—Ph Me V^(a) Me Me 3-Cl—PhMe V^(b) Me Me 3-Cl—Ph Me V^(c) Me Me 3-Cl—Ph Me V^(d) Me Me 3-Cl—Ph MeV^(e) Me Me 3-Cl—Ph Me V^(f) Me Me 3-Cl—Ph Me V^(g) Me Me 3-Cl—Ph MeV^(h) Me Me 3-Cl—Ph Me —CH₂OC(═O)CH₂— Me Me 3-Cl—Ph Me —CH₂C(═O)CH₂— MeMe 3-Cl—Ph Me —CH₂C(═O)— Me Me 3-Cl—Ph Me —CH₂— Me Me c-Pr Me —CH₂CH₂—Me Me c-Pr Me —CH₂CH₂CH₂— Me Me c-Pr Me —CH₂CH₂CH₂CH₂— Me Me c-Pr Me—CH₂OCH₂CH₂— Me Me c-Pr Me —CH₂CH₂OCH₂— Me Me c-Pr Me —CH₂C(═O)CH₂CH₂—Me Me c-Pr Me —CH₂CH₂C(═O)CH₂— Me Me c-Pr Me —CH₂C(═S)CH₂CH₂— Me Me c-PrMe —CH₂CH₂C(═S)CH₂— Me Me c-Pr Me —CH₂C(═O)CH₂— Me Me c-Pr Me—CH₂C(═S)CH₂— Me Me c-Pr Me —CH(Me)— Me Me c-Pr Me —CH(OMe)— Me Me c-PrMe —CH(Me)CH₂— Me Me c-Pr Me —CH₂CH(Me)— Me Me c-Pr Me —CH₂CH(OMe)— MeMe c-Pr Me —CH(Me)CH₂CH₂— Me Me c-Pr Me —CH₂CH(Me)CH₂— Me Me c-Pr Me—CH₂CH₂CH(Me)— Me Me c-Pr Me —CH(Et)— Me Me c-Pr Me —CH(Et)CH₂— Me Mec-Pr F —CH₂— Me Me Me F —CH₂CH₂— Me Me Me F —CH₂CH₂CH₂— Me Me Me F—CH₂CH₂CH₂CH₂— Me Me Me F —CH₂OCH₂CH₂— Me Me Me F —CH₂CH₂OCH₂— Me Me MeF —CH₂C(═O)CH₂CH₂— Me Me Me F —CH₂CH₂C(═O)CH₂— Me Me Me F—CH₂C(═S)CH₂CH₂— Me Me Me F —CH₂CH₂C(═S)CH₂— Me Me Me F —CH₂C(═O)CH₂— MeMe Me F —CH₂C(═S)CH₂— Me Me Me F —CH(Me)— Me Me Me F —CH(OMe)— Me Me MeF —CH(Me)CH₂— Me Me Me F —CH₂CH(Me)— Me Me Me F —CH₂CH(OMe)— Me Me Me F—CH(Me)CH₂CH₂— Me Me Me F —CH₂CH(Me)CH₂— Me Me Me F —CH₂CH₂CH(Me)— Me MeMe F —CH(Et)— Me Me Me F —CH(Et)CH₂— Me Me Me F —CH₂CH(Et)— Me Me Me F—CH(Et)CH₂CH₂— Me Me Me F —CH₂CH(Et)CH₂— Me Me Me F —CH₂CH₂CH(Et)— Me MeMe F —CH(OCF₃)— Me Me Me F —CH(CF₃)— Me Me Me F —CH₂CF₂CH₂— Me Me Me F—CH₂CHFCH₂— Me Me Me F —CH₂CF₂— Me Me Me F —CH₂CHF— Me Me Me F —CH(CN)—Me Me Me F V^(a) Me Me Me F V^(b) Me Me Me F V^(c) Me Me Me F V^(d) MeMe Me F V^(e) Me Me Me F V^(f) Me Me Me F V^(g) Me Me Me F V^(h) Me MeMe F —CH₂OC(═O)CH₂— Me Me Me F —CH₂C(═O)CH₂— Me Me Me F —CH₂C(═O)— Me MeMe F —CH₂— Me Me Et F —CH₂CH₂— Me Me Et F —CH₂CH₂CH₂— Me Me Et F—CH₂CH₂CH₂CH₂— Me Me Et F —CH₂OCH₂CH₂— Me Me Et F —CH₂CH₂OCH₂— Me Me EtF —CH₂C(═O)CH₂CH₂— Me Me Et F —CH₂CH₂C(═O)CH₂— Me Me Et F—CH₂C(═S)CH₂CH₂— Me Me Et F —CH₂CH₂C(═S)CH₂— Me Me Et F —CH₂C(═O)CH₂— MeMe Et F —CH₂C(═S)CH₂— Me Me Et F —CH(Me)— Me Me Et F —CH(OMe)— Me Me EtF —CH(Me)CH₂— Me Me Et F —CH₂CH(Me)— Me Me Et F —CH₂CH(OMe)— Me Me Et F—CH(Me)CH₂CH₂— Me Me Et F —CH₂CH(Me)CH₂— Me Me Et F —CH₂CH₂CH(Me)— Me MeEt F —CH(Et)— Me Me Et F —CH(Et)CH₂— Me Me Et F —CH₂CH(Et)— Me Me Et F—CH(Et)CH₂CH₂— Me Me Et F —CH₂CH(Et)CH₂— Me Me Et F —CH₂CH₂CH(Et)— Me MeEt F —CH(OCF₃)— Me Me Et F —CH(CF₃)— Me Me Et F —CH₂CF₂CH₂— Me Me Et F—CH₂CHFCH₂— Me Me Et F —CH₂CF₂— Me Me Et F —CH₂CHF— Me Me Et F —CH(CN)—Me Me Et F V^(a) Me Me Et F V^(b) Me Me Et F V^(c) Me Me Et F V^(d) MeMe Et F V^(e) Me Me Et F V^(f) Me Me Et F V^(g) Me Me Et F V^(h) Me MeEt F —CH₂OC(═O)CH₂— Me Me Et F —CH₂C(═O)CH₂— Me Me Et F —CH₂C(═O)— Me MeEt F —CH₂— Me Et Et F —CH₂CH₂— Me Et Et F —CH₂CH₂CH₂— Me Et Et F—CH₂CH₂CH₂CH₂— Me Et Et F —CH₂OCH₂CH₂— Me Et Et F —CH₂CH₂OCH₂— Me Et EtF —CH₂C(═O)CH₂CH₂— Me Et Et F —CH₂CH₂C(═O)CH₂— Me Et Et F—CH₂C(═S)CH₂CH₂— Me Et Et F —CH₂CH₂C(═S)CH₂— Me Et Et F —CH₂C(═O)CH₂— MeEt Et F —CH₂C(═S)CH₂— Me Et Et F —CH(Me)— Me Et Et F —CH(OMe)— Me Et EtF —CH(Me)CH₂— Me Et Et F —CH₂CH(Me)— Me Et Et F —CH₂CH(OMe)— Me Et Et F—CH(Me)CH₂CH₂— Me Et Et F —CH₂CH(Me)CH₂— Me Et Et F —CH₂CH₂CH(Me)— Me EtEt F —CH(Et)— Me Et Et F —CH(Et)CH₂— Me Et Et F —CH₂CH(Et)— Me Et Et F—CH(Et)CH₂CH₂— Me Et Et F —CH₂CH(Et)CH₂— Me Et Et F —CH₂CH₂CH(Et)— Me EtEt F —CH(OCF₃)— Me Et Et F —CH(CF₃)— Me Et Et F —CH₂CF₂CH₂— Me Et Et F—CH₂CHFCH₂— Me Et Et F —CH₂CF₂— Me Et Et F —CH₂CHF— Me Et Et F —CH(CN)—Me Et Et F V^(a) Me Et Et F V^(b) Me Et Et F V^(c) Me Et Et F V^(d) MeEt Et F V^(e) Me Et Et F V^(f) Me Et Et F V^(g) Me Et Et F V^(h) Me EtEt F —CH₂OC(═O)CH₂— Me Et Et F —CH₂C(═O)CH₂— Me Et Et F —CH₂C(═O)— Me EtEt F —CH₂— Et Et Et F —CH₂CH₂— Et Et Et F —CH₂CH₂CH₂— Et Et Et F—CH₂CH₂CH₂CH₂— Et Et Et F —CH₂OCH₂CH₂— Et Et Et F —CH₂CH₂OCH₂— Et Et EtF —CH₂C(═O)CH₂CH₂— Et Et Et F —CH₂CH₂C(═O)CH₂— Et Et Et F—CH₂C(═S)CH₂CH₂— Et Et Et F —CH₂CH₂C(═S)CH₂— Et Et Et F —CH₂C(═O)CH₂— EtEt Et F —CH₂C(═S)CH₂— Et Et Et F —CH(Me)— Et Et Et F —CH(OMe)— Et Et EtF —CH(Me)CH₂— Et Et Et F —CH₂CH(Me)— Et Et Et F —CH₂CH(OMe)— Et Et Et F—CH(Me)CH₂CH₂— Et Et Et F —CH₂CH(Me)CH₂— Et Et Et F —CH₂CH₂CH(Me)— Et EtEt F —CH(Et)— Et Et Et F —CH(Et)CH₂— Et Et Et F —CH₂CH(Et)— Et Et Et F—CH(Et)CH₂CH₂— Et Et Et F —CH₂CH(Et)CH₂— Et Et Et F —CH₂CH₂CH(Et)— Et EtEt F —CH(OCF₃)— Et Et Et F —CH(CF₃)— Et Et Et F —CH₂CF₂CH₂— Et Et Et F—CH₂CHFCH₂— Et Et Et F —CH₂CF₂— Et Et Et F —CH₂CHF— Et Et Et F —CH(CN)—Et Et Et F V^(a) Et Et Et F V^(b) Et Et Et F V^(c) Et Et Et F V^(d) EtEt Et F V^(e) Et Et Et F V^(f) Et Et Et F V^(g) Et Et Et F V^(h) Et EtEt F —CH₂OC(═O)CH₂— Et Et Et F —CH₂C(═O)CH₂— Et Et Et F —CH₂C(═O)— Et EtEt F —CH₂— Me Me i-Pr F —CH₂CH₂— Me Me i-Pr F —CH₂CH₂CH₂— Me Me i-Pr F—CH₂CH₂CH₂CH₂— Me Me i-Pr F —CH₂OCH₂CH₂— Me Me i-Pr F —CH₂CH₂OCH₂— Me Mei-Pr F —CH₂C(═O)CH₂CH₂— Me Me i-Pr F —CH₂CH₂C(═O)CH₂— Me Me i-Pr F—CH₂C(═S)CH₂CH₂— Me Me i-Pr F —CH₂CH₂C(═S)CH₂— Me Me i-Pr F—CH₂C(═O)CH₂— Me Me i-Pr F —CH₂C(═S)CH₂— Me Me i-Pr F —CH(Me)— Me Mei-Pr F —CH(OMe)— Me Me i-Pr F —CH(Me)CH₂— Me Me i-Pr F —CH₂CH(Me)— Me Mei-Pr F —CH₂CH(OMe)— Me Me i-Pr F —CH(Me)CH₂CH₂— Me Me i-Pr F—CH₂CH(Me)CH₂— Me Me i-Pr F —CH₂CH₂CH(Me)— Me Me i-Pr F —CH(Et)— Me Mei-Pr F —CH(Et)CH₂— Me Me i-Pr F —CH₂CH(Et)— Me Me i-Pr F —CH(Et)CH₂CH₂—Me Me i-Pr F —CH₂CH(Et)CH₂— Me Me i-Pr F —CH₂CH₂CH(Et)— Me Me i-Pr F—CH(OCF₃)— Me Me i-Pr F —CH(CF₃)— Me Me i-Pr F —CH₂CF₂CH₂— Me Me i-Pr F—CH₂CHFCH₂— Me Me i-Pr F —CH₂CF₂— Me Me i-Pr F —CH₂CHF— Me Me i-Pr F—CH(CN)— Me Me i-Pr F V^(a) Me Me i-Pr F V^(b) Me Me i-Pr F V^(c) Me Mei-Pr F V^(d) Me Me i-Pr F V^(e) Me Me i-Pr F V^(f) Me Me i-Pr F V^(g) MeMe i-Pr F V^(h) Me Me i-Pr F —CH₂OC(═O)CH₂— Me Me i-Pr F —CH₂C(═O)CH₂—Me Me i-Pr F —CH₂C(═O)— Me Me i-Pr F —CH₂— Me Et i-Pr F —CH₂CH₂— Me Eti-Pr F —CH₂CH₂CH₂— Me Et i-Pr F —CH₂CH₂CH₂CH₂— Me Et i-Pr F —CH₂OCH₂CH₂—Me Et i-Pr F —CH₂CH₂OCH₂— Me Et i-Pr F —CH₂C(═O)CH₂CH₂— Me Et i-Pr F—CH₂CH₂C(═O)CH₂— Me Et i-Pr F —CH₂C(═S)CH₂CH₂— Me Et i-Pr F—CH₂CH₂C(═S)CH₂— Me Et i-Pr F —CH₂C(═O)CH₂— Me Et i-Pr F —CH₂C(═S)CH₂—Me Et i-Pr F —CH(Me)— Me Et i-Pr F —CH(OMe)— Me Et i-Pr F —CH(Me)CH₂— MeEt i-Pr F —CH₂CH(Me)— Me Et i-Pr F —CH₂CH(OMe)— Me Et i-Pr F—CH(Me)CH₂CH₂— Me Et i-Pr F —CH₂CH(Me)CH₂— Me Et i-Pr F —CH₂CH₂CH(Me)—Me Et i-Pr F —CH(Et)— Me Et i-Pr F —CH(Et)CH₂— Me Et i-Pr F —CH₂CH(Et)—Me Et i-Pr F —CH(Et)CH₂CH₂— Me Et i-Pr F —CH₂CH(Et)CH₂— Me Et i-Pr F—CH₂CH₂CH(Et)— Me Et i-Pr F —CH(OCF₃)— Me Et i-Pr F —CH(CF₃)— Me Et i-PrF —CH₂CF₂CH₂— Me Et i-Pr F —CH₂CHFCH₂— Me Et i-Pr F —CH₂CF₂— Me Et i-PrF —CH₂CHF— Me Et i-Pr F —CH(CN)— Me Et i-Pr F V^(a) Me Et i-Pr F V^(b)Me Et i-Pr F V^(c) Me Et i-Pr F V^(d) Me Et i-Pr F V^(e) Me Et i-Pr FV^(f) Me Et i-Pr F V^(g) Me Et i-Pr F V^(h) Me Et i-Pr F —CH₂OC(═O)CH₂—Me Et i-Pr F —CH₂C(═O)CH₂— Me Et i-Pr F —CH₂C(═O)— Me Et i-Pr F —CH₂— MeMe Ph F —CH₂CH₂— Me Me Ph F —CH₂CH₂CH₂— Me Me Ph F —CH₂CH₂CH₂CH₂— Me MePh F —CH₂OCH₂CH₂— Me Me Ph F —CH₂CH₂OCH₂— Me Me Ph F —CH₂C(═O)CH₂CH₂— MeMe Ph F —CH₂CH₂C(═O)CH₂— Me Me Ph F —CH₂C(═S)CH₂CH₂— Me Me Ph F—CH₂CH₂C(═S)CH₂— Me Me Ph F —CH₂C(═O)CH₂— Me Me Ph F —CH₂C(═S)CH₂— Me MePh F —CH(Me)— Me Me Ph F —CH(OMe)— Me Me Ph F —CH(Me)CH₂— Me Me Ph F—CH₂CH(Me)— Me Me Ph F —CH₂CH(OMe)— Me Me Ph F —CH(Me)CH₂CH₂— Me Me Ph F—CH₂CH(Me)CH₂— Me Me Ph F —CH₂CH₂CH(Me)— Me Me Ph F —CH(Et)— Me Me Ph F—CH(Et)CH₂— Me Me Ph F —CH₂CH(Et)— Me Me Ph F —CH(Et)CH₂CH₂— Me Me Ph F—CH₂CH(Et)CH₂— Me Me Ph F —CH₂CH₂CH(Et)— Me Me Ph F —CH(OCF₃)— Me Me PhF —CH(CF₃)— Me Me Ph F —CH₂CF₂CH₂— Me Me Ph F —CH₂CHFCH₂— Me Me Ph F—CH₂CF₂— Me Me Ph F —CH₂CHF— Me Me Ph F —CH(CN)— Me Me Ph F V^(a) Me MePh F V^(b) Me Me Ph F V^(c) Me Me Ph F V^(d) Me Me Ph F V^(e) Me Me Ph FV^(f) Me Me Ph F V^(g) Me Me Ph F V^(h) Me Me Ph F —CH₂OC(═O)CH₂— Me MePh F —CH₂C(═O)CH₂— Me Me Ph F —CH₂C(═O)— Me Me Ph F —CH₂— Me Me 4-Cl—PhF —CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH₂CH₂— MeMe 4-Cl—Ph F —CH₂OCH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂OCH₂— Me Me 4-Cl—Ph F—CH₂C(═O)CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂C(═O)CH₂— Me Me 4-Cl—Ph F—CH₂C(═S)CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂C(═S)CH₂— Me Me 4-Cl—Ph F—CH₂C(═O)CH₂— Me Me 4-Cl—Ph F —CH₂C(═S)CH₂— Me Me 4-Cl—Ph F —CH(Me)— MeMe 4-Cl—Ph F —CH(OMe)— Me Me 4-Cl—Ph F —CH(Me)CH₂— Me Me 4-Cl—Ph F—CH₂CH(Me)— Me Me 4-Cl—Ph F —CH₂CH(OMe)— Me Me 4-Cl—Ph F —CH(Me)CH₂CH₂—Me Me 4-Cl—Ph F —CH₂CH(Me)CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH(Me)— Me Me4-Cl—Ph F —CH(Et)— Me Me 4-Cl—Ph F —CH(Et)CH₂— Me Me 4-Cl—Ph F—CH₂CH(Et)— Me Me 4-Cl—Ph F —CH(Et)CH₂CH₂— Me Me 4-Cl—Ph F—CH₂CH(Et)CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH(Et)— Me Me 4-Cl—Ph F —CH(OCF₃)—Me Me 4-Cl—Ph F —CH(CF₃)— Me Me 4-Cl—Ph F —CH₂CF₂CH₂— Me Me 4-Cl—Ph F—CH₂CHFCH₂— Me Me 4-Cl—Ph F —CH₂CF₂— Me Me 4-Cl—Ph F —CH₂CHF— Me Me4-Cl—Ph F —CH(CN)— Me Me 4-Cl—Ph F V^(a) Me Me 4-Cl—Ph F V^(b) Me Me4-Cl—Ph F V^(c) Me Me 4-Cl—Ph F V^(d) Me Me 4-Cl—Ph F V^(e) Me Me4-Cl—Ph F V^(f) Me Me 4-Cl—Ph F V^(g) Me Me 4-Cl—Ph F V^(h) Me Me4-Cl—Ph F —CH₂OC(═O)CH₂— Me Me 4-Cl—Ph F —CH₂C(═O)CH₂— Me Me 4-Cl—Ph F—CH₂C(═O)— Me Me 4-Cl—Ph F —CH₂— Me Me 3-Cl—Ph F —CH₂CH₂— Me Me 3-Cl—PhF —CH₂CH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂CH₂CH₂— Me Me 3-Cl—Ph F—CH₂OCH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂OCH₂— Me Me 3-Cl—Ph F—CH₂C(═O)CH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂C(═O)CH₂— Me Me 3-Cl—Ph F—CH₂C(═S)CH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂C(═S)CH₂— Me Me 3-Cl—Ph F—CH₂C(═O)CH₂— Me Me 3-Cl—Ph F —CH₂C(═S)CH₂— Me Me 3-Cl—Ph F —CH(Me)— MeMe 3-Cl—Ph F —CH(OMe)— Me Me 3-Cl—Ph F —CH(Me)CH₂— Me Me 3-Cl—Ph F—CH₂CH(Me)— Me Me 3-Cl—Ph F —CH₂CH(OMe)— Me Me 3-Cl—Ph F —CH(Me)CH₂CH₂—Me Me 3-Cl—Ph F —CH₂CH(Me)CH₂— Me Me 3-Cl—Ph F —CH₂CH₂CH(Me)— Me Me3-Cl—Ph F —CH(Et)— Me Me 3-Cl—Ph F —CH(Et)CH₂— Me Me 3-Cl—Ph F—CH₂CH(Et)— Me Me 3-Cl—Ph F —CH(Et)CH₂CH₂— Me Me 3-Cl—Ph F—CH₂CH(Et)CH₂— Me Me 3-Cl—Ph F —CH₂CH₂CH(Et)— Me Me 3-Cl—Ph F —CH(OCF₃)—Me Me 3-Cl—Ph F —CH(CF₃)— Me Me 3-Cl—Ph F —CH₂CF₂CH₂— Me Me 3-Cl—Ph F—CH₂CHFCH₂— Me Me 3-Cl—Ph F —CH₂CF₂— Me Me 3-Cl—Ph F —CH₂CHF— Me Me3-Cl—Ph F —CH(CN)— Me Me 3-Cl—Ph F V^(a) Me Me 3-Cl—Ph F V^(b) Me Me3-Cl—Ph F V^(c) Me Me 3-Cl—Ph F V^(d) Me Me 3-Cl—Ph F V^(e) Me Me3-Cl—Ph F V^(f) Me Me 3-Cl—Ph F V^(g) Me Me 3-Cl—Ph F V^(h) Me Me3-Cl—Ph F —CH₂OC(═O)CH₂— Me Me 3-Cl—Ph F —CH₂C(═O)CH₂— Me Me 3-Cl—Ph F—CH₂C(═O)— Me Me 3-Cl—Ph F —CH₂— Me Me 2-Cl—Ph F —CH₂CH₂— Me Me 2-Cl—PhF —CH₂CH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂CH₂CH₂— Me Me 2-Cl—Ph F—CH₂OCH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂OCH₂— Me Me 2-Cl—Ph F—CH₂C(═O)CH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂C(═O)CH₂— Me Me 2-Cl—Ph F—CH₂C(═S)CH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂C(═S)CH₂— Me Me 2-Cl—Ph F—CH₂C(═O)CH₂— Me Me 2-Cl—Ph F —CH₂C(═S)CH₂— Me Me 2-Cl—Ph F —CH(Me)— MeMe 2-Cl—Ph F —CH(OMe)— Me Me 2-Cl—Ph F —CH(Me)CH₂— Me Me 2-Cl—Ph F—CH₂CH(Me)— Me Me 2-Cl—Ph F —CH₂CH(OMe)— Me Me 2-Cl—Ph F —CH(Me)CH₂CH₂—Me Me 2-Cl—Ph F —CH₂CH(Me)CH₂— Me Me 2-Cl—Ph F —CH₂CH₂CH(Me)— Me Me2-Cl—Ph F —CH(Et)— Me Me 2-Cl—Ph F —CH(Et)CH₂— Me Me 2-Cl—Ph F—CH₂CH(Et)— Me Me 2-Cl—Ph F —CH(Et)CH₂CH₂— Me Me 2-Cl—Ph F—CH₂CH(Et)CH₂— Me Me 2-Cl—Ph F —CH₂CH₂CH(Et)— Me Me 2-Cl—Ph F —CH(OCF₃)—Me Me 2-Cl—Ph F —CH(CF₃)— Me Me 2-Cl—Ph F —CH₂CF₂CH₂— Me Me 2-Cl—Ph F—CH₂CHFCH₂— Me Me 2-Cl—Ph F —CH₂CF₂— Me Me 2-Cl—Ph F —CH₂CHF— Me Me2-Cl—Ph F —CH(CN)— Me Me 2-Cl—Ph F V^(a) Me Me 2-Cl—Ph F V^(b) Me Me2-Cl—Ph F V^(c) Me Me 2-Cl—Ph F V^(d) Me Me 2-Cl—Ph F V^(e) Me Me2-Cl—Ph F V^(f) Me Me 2-Cl—Ph F V^(g) Me Me 2-Cl—Ph F V^(h) Me Me2-Cl—Ph F —CH₂OC(═O)CH₂— Me Me 2-Cl—Ph F —CH₂C(═O)CH₂— Me Me 2-Cl—Ph F—CH₂C(═O)— Me Me 2-Cl—Ph F —CH₂— Me Me c-Pr F —CH₂CH₂— Me Me c-Pr F—CH₂CH₂CH₂— Me Me c-Pr F —CH₂CH₂CH₂CH₂— Me Me c-Pr F —CH₂OCH₂CH₂— Me Mec-Pr F —CH₂CH₂OCH₂— Me Me c-Pr F —CH₂C(═O)CH₂CH₂— Me Me c-Pr F—CH₂CH₂C(═O)CH₂— Me Me c-Pr F —CH₂C(═S)CH₂CH₂— Me Me c-Pr F—CH₂CH₂C(═S)CH₂— Me Me c-Pr F —CH₂C(═O)CH₂— Me Me c-Pr F —CH₂C(═S)CH₂—Me Me c-Pr F —CH(Me)— Me Me c-Pr F —CH(OMe)— Me Me c-Pr F —CH(Me)CH₂— MeMe c-Pr F —CH₂CH(Me)— Me Me c-Pr F —CH₂CH(OMe)— Me Me c-Pr F—CH(Me)CH₂CH₂— Me Me c-Pr F —CH₂CH(Me)CH₂— Me Me c-Pr F —CH₂CH₂CH(Me)—Me Me c-Pr F —CH(Et)— Me Me c-Pr F —CH(Et)CH₂— Me Me c-Pr F —CH₂CH(Et)—Me Me c-Pr F —CH(Et)CH₂CH₂— Me Me c-Pr F —CH₂CH(Et)CH₂— Me Me c-Pr F—CH₂CH₂CH(Et)— Me Me c-Pr F —CH(OCF₃)— Me Me c-Pr F —CH(CF₃)— Me Me c-PrF —CH₂CF₂CH₂— Me Me c-Pr F —CH₂CHFCH₂— Me Me c-Pr F —CH₂CF₂— Me Me c-PrF —CH₂CHF— Me Me c-Pr F —CH(CN)— Me Me c-Pr F V^(a) Me Me c-Pr F V^(b)Me Me c-Pr F V^(c) Me Me c-Pr F V^(d) Me Me c-Pr F V^(e) Me Me c-Pr FV^(f) Me Me c-Pr F V^(g) Me Me c-Pr F V^(h) Me Me c-Pr F —CH₂OC(═O)CH₂—Me Me c-Pr F —CH₂C(═O)CH₂— Me Me c-Pr F —CH₂C(═O)— Me Me c-Pr Me —CH₂—Me Me Et Me —CH₂CH₂— Me Me Et Me —CH₂CH₂CH₂— Me Me Et Me —CH₂CH₂CH₂CH₂—Me Me Et Me —CH₂OCH₂CH₂— Me Me Et Me —CH₂CH₂OCH₂— Me Me Et Me—CH₂C(═O)CH₂CH₂— Me Me Et Me —CH₂CH₂C(═O)CH₂— Me Me Et Me—CH₂C(═S)CH₂CH₂— Me Me Et Me —CH₂CH₂C(═S)CH₂— Me Me Et Me —CH₂C(═O)CH₂—Me Me Et Me —CH₂C(═S)CH₂— Me Me Et Me —CH(Me)— Me Me Et Me —CH(OMe)— MeMe Et Me —CH(Me)CH₂— Me Me Et Me —CH₂CH(Me)— Me Me Et Me —CH₂CH(OMe)— MeMe Et Me —CH(Me)CH₂CH₂— Me Me Et Me —CH₂CH(Me)CH₂— Me Me Et Me—CH₂CH₂CH(Me)— Me Me Et Me —CH(Et)— Me Me Et Me —CH(Et)CH₂— Me Me Et Me—CH₂CH(Et)— Me Me Et Me —CH(Et)CH₂CH₂— Me Me Et Me —CH₂CH(Et)CH₂— Me MeEt Me —CH₂CH₂CH(Et)— Me Me Et Me —CH(OCF₃)— Me Me Et Me —CH(CF₃)— Me MeEt Me —CH₂CF₂CH₂— Me Me Et Me —CH₂CHFCH₂— Me Me Et Me —CH₂CF₂— Me Me EtMe —CH₂CHF— Me Me Et Me —CH(CN)— Me Me Et Me V^(a) Me Me Et Me V^(b) MeMe Et Me V^(c) Me Me Et Me V^(d) Me Me Et Me V^(e) Me Me Et Me V^(f) MeMe Et Me V^(g) Me Me Et Me V^(h) Me Me Et Me —CH₂OC(═O)CH₂— Me Me Et Me—CH₂C(═O)CH₂— Me Me Et Me —CH₂C(═O)— Me Me Et Me —CH₂— Et Et Et Me—CH₂CH₂— Et Et Et Me —CH₂CH₂CH₂— Et Et Et Me —CH₂CH₂CH₂CH₂— Et Et Et Me—CH₂OCH₂CH₂— Et Et Et Me —CH₂CH₂OCH₂— Et Et Et Me —CH₂C(═O)CH₂CH₂— Et EtEt Me —CH₂CH₂C(═O)CH₂— Et Et Et Me —CH₂C(═S)CH₂CH₂— Et Et Et Me—CH₂CH₂C(═S)CH₂— Et Et Et Me —CH₂C(═O)CH₂— Et Et Et Me —CH₂C(═S)CH₂— EtEt Et Me —CH(Me)— Et Et Et Me —CH(OMe)— Et Et Et Me —CH(Me)CH₂— Et Et EtMe —CH₂CH(Me)— Et Et Et Me —CH₂CH(OMe)— Et Et Et Me —CH(Me)CH₂CH₂— Et EtEt Me —CH₂CH(Me)CH₂— Et Et Et Me —CH₂CH₂CH(Me)— Et Et Et Me —CH(Et)— EtEt Et Me —CH(Et)CH₂— Et Et Et Me —CH₂CH(Et)— Et Et Et Me —CH(Et)CH₂CH₂—Et Et Et Me —CH₂CH(Et)CH₂— Et Et Et Me —CH₂CH₂CH(Et)— Et Et Et Me—CH(OCF₃)— Et Et Et Me —CH(CF₃)— Et Et Et Me —CH₂CF₂CH₂— Et Et Et Me—CH₂CHFCH₂— Et Et Et Me —CH₂CF₂— Et Et Et Me —CH₂CHF— Et Et Et Me—CH(CN)— Et Et Et Me V^(a) Et Et Et Me V^(b) Et Et Et Me V^(c) Et Et EtMe V^(d) Et Et Et Me V^(e) Et Et Et Me V^(f) Et Et Et Me V^(g) Et Et EtMe V^(h) Et Et Et Me —CH₂OC(═O)CH₂— Et Et Et Me —CH₂C(═O)CH₂— Et Et EtMe —CH₂C(═O)— Et Et Et Me —CH₂— Me Et i-Pr Me —CH₂CH₂— Me Et i-Pr Me—CH₂CH₂CH₂— Me Et i-Pr Me —CH₂CH₂CH₂CH₂— Me Et i-Pr Me —CH₂OCH₂CH₂— MeEt i-Pr Me —CH₂CH₂OCH₂— Me Et i-Pr Me —CH₂C(═O)CH₂CH₂— Me Et i-Pr Me—CH₂CH₂C(═O)CH₂— Me Et i-Pr Me —CH₂C(═S)CH₂CH₂— Me Et i-Pr Me—CH₂CH₂C(═S)CH₂— Me Et i-Pr Me —CH₂C(═O)CH₂— Me Et i-Pr Me —CH₂C(═S)CH₂—Me Et i-Pr Me —CH(Me)— Me Et i-Pr Me —CH(OMe)— Me Et i-Pr Me —CH(Me)CH₂—Me Et i-Pr Me —CH₂CH(Me)— Me Et i-Pr Me —CH₂CH(OMe)— Me Et i-Pr Me—CH(Me)CH₂CH₂— Me Et i-Pr Me —CH₂CH(Me)CH₂— Me Et i-Pr Me —CH₂CH₂CH(Me)—Me Et i-Pr Me —CH(Et)— Me Et i-Pr Me —CH(Et)CH₂— Me Et i-Pr Me—CH₂CH(Et)— Me Et i-Pr Me —CH(Et)CH₂CH₂— Me Et i-Pr Me —CH₂CH(Et)CH₂— MeEt i-Pr Me —CH₂CH₂CH(Et)— Me Et i-Pr Me —CH(OCF₃)— Me Et i-Pr Me—CH(CF₃)— Me Et i-Pr Me —CH₂CF₂CH₂— Me Et i-Pr Me —CH₂CHFCH₂— Me Et i-PrMe —CH₂CF₂— Me Et i-Pr Me —CH₂CHF— Me Et i-Pr Me —CH(CN)— Me Et i-Pr MeV^(a) Me Et i-Pr Me V^(b) Me Et i-Pr Me V^(c) Me Et i-Pr Me V^(d) Me Eti-Pr Me V^(e) Me Et i-Pr Me V^(f) Me Et i-Pr Me V^(g) Me Et i-Pr MeV^(h) Me Et i-Pr Me —CH₂OC(═O)CH₂— Me Et i-Pr Me —CH₂C(═O)CH₂— Me Eti-Pr Me —CH₂C(═O)— Me Et i-Pr Me —CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂— Me Me4-Cl—Ph Me —CH₂CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂CH₂CH₂— Me Me 4-Cl—Ph Me—CH₂OCH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂OCH₂— Me Me 4-Cl—Ph Me—CH₂C(═O)CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂C(═O)CH₂— Me Me 4-Cl—Ph Me—CH₂C(═S)CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂C(═S)CH₂— Me Me 4-Cl—Ph Me—CH₂C(═O)CH₂— Me Me 4-Cl—Ph Me —CH₂C(═S)CH₂— Me Me 4-Cl—Ph Me —CH(Me)—Me Me 4-Cl—Ph Me —CH(OMe)— Me Me 4-Cl—Ph Me —CH(Me)CH₂— Me Me 4-Cl—Ph Me—CH₂CH(Me)— Me Me 4-Cl—Ph Me —CH₂CH(OMe)— Me Me 4-Cl—Ph Me—CH(Me)CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH(Me)CH₂— Me Me 4-Cl—Ph Me—CH₂CH₂CH(Me)— Me Me 4-Cl—Ph Me —CH(Et)— Me Me 4-Cl—Ph Me —CH(Et)CH₂— MeMe 4-Cl—Ph Me —CH₂CH(Et)— Me Me 4-Cl—Ph Me —CH(Et)CH₂CH₂— Me Me 4-Cl—PhMe —CH₂CH(Et)CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂CH(Et)— Me Me 4-Cl—Ph Me—CH(OCF₃)— Me Me 4-Cl—Ph Me —CH(CF₃)— Me Me 4-Cl—Ph Me —CH₂CF₂CH₂— Me Me4-Cl—Ph Me —CH₂CHFCH₂— Me Me 4-Cl—Ph Me —CH₂CF₂— Me Me 4-Cl—Ph Me—CH₂CHF— Me Me 4-Cl—Ph Me —CH(CN)— Me Me 4-Cl—Ph Me V^(a) Me Me 4-Cl—PhMe V^(b) Me Me 4-Cl—Ph Me V^(c) Me Me 4-Cl—Ph Me V^(d) Me Me 4-Cl—Ph MeV^(e) Me Me 4-Cl—Ph Me V^(f) Me Me 4-Cl—Ph Me V^(g) Me Me 4-Cl—Ph MeV^(h) Me Me 4-Cl—Ph Me —CH₂OC(═O)CH₂— Me Me 4-Cl—Ph Me —CH₂C(═O)CH₂— MeMe 4-Cl—Ph Me —CH₂C(═O)— Me Me 4-Cl—Ph Me —CH₂— Me Me 2-Cl—Ph Me—CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂CH₂CH₂— MeMe 2-Cl—Ph Me —CH₂OCH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂OCH₂— Me Me 2-Cl—PhMe —CH₂C(═O)CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂C(═O)CH₂— Me Me 2-Cl—Ph Me—CH₂C(═S)CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂C(═S)CH₂— Me Me 2-Cl—Ph Me—CH₂C(═O)CH₂— Me Me 2-Cl—Ph Me —CH₂C(═S)CH₂— Me Me 2-Cl—Ph Me —CH(Me)—Me Me 2-Cl—Ph Me —CH(OMe)— Me Me 2-Cl—Ph Me —CH(Me)CH₂— Me Me 2-Cl—Ph Me—CH₂CH(Me)— Me Me 2-Cl—Ph Me —CH₂CH(OMe)— Me Me 2-Cl—Ph Me—CH(Me)CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH(Me)CH₂— Me Me 2-Cl—Ph Me—CH₂CH₂CH(Me)— Me Me 2-Cl—Ph Me —CH(Et)— Me Me 2-Cl—Ph Me —CH(Et)CH₂— MeMe 2-Cl—Ph Me —CH₂CH(Et)— Me Me 2-Cl—Ph Me —CH(Et)CH₂CH₂— Me Me 2-Cl—PhMe —CH₂CH(Et)CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂CH(Et)— Me Me 2-Cl—Ph Me—CH(OCF₃)— Me Me 2-Cl—Ph Me —CH(CF₃)— Me Me 2-Cl—Ph Me —CH₂CF₂CH₂— Me Me2-Cl—Ph Me —CH₂CHFCH₂— Me Me 2-Cl—Ph Me —CH₂CF₂— Me Me 2-Cl—Ph Me—CH₂CHF— Me Me 2-Cl—Ph Me —CH(CN)— Me Me 2-Cl—Ph Me V^(a) Me Me 2-Cl—PhMe V^(b) Me Me 2-Cl—Ph Me V^(c) Me Me 2-Cl—Ph Me V^(d) Me Me 2-Cl—Ph MeV^(e) Me Me 2-Cl—Ph Me V^(f) Me Me 2-Cl—Ph Me V^(g) Me Me 2-Cl—Ph MeV^(h) Me Me 2-Cl—Ph Me —CH₂OC(═O)CH₂— Me Me 2-Cl—Ph Me —CH₂C(═O)CH₂— MeMe 2-Cl—Ph Me —CH₂C(═O)— Me Me 2-Cl—Ph Me —CH₂CH(Et)— Me Me c-Pr Me—CH(Et)CH₂CH₂— Me Me c-Pr Me —CH₂CH(Et)CH₂— Me Me c-Pr Me —CH₂CH₂CH(Et)—Me Me c-Pr Me —CH(OCF₃)— Me Me c-Pr Me —CH(CF₃)— Me Me c-Pr Me—CH₂CF₂CH₂— Me Me c-Pr Me —CH₂CHFCH₂— Me Me c-Pr Me —CH₂CF₂— Me Me c-PrMe —CH₂CHF— Me Me c-Pr Me —CH(CN)— Me Me c-Pr Me V^(a) Me Me c-Pr MeV^(b) Me Me c-Pr Me V^(c) Me Me c-Pr Me V^(d) Me Me c-Pr Me V^(e) Me Mec-Pr Me V^(f) Me Me c-Pr Me V^(g) Me Me c-Pr Me V^(h) Me Me c-Pr Me—CH₂OC(═O)CH₂— Me Me c-Pr Me —CH₂C(═O)CH₂— Me Me c-Pr Me —CH₂C(═O)— MeMe c-Pr

TABLE 2

R¹ V¹ R^(10a) R^(10b) R^(10c) Cl —CH₂— Me Me Me Cl —CH₂CH₂— Me Me Me Cl—CH₂CH₂CH₂— Me Me Me Cl —CH₂CH₂CH₂CH₂— Me Me Me Cl —CH₂OCH₂CH₂— Me Me MeCl —CH₂CH₂OCH₂— Me Me Me Cl —CH₂C(═O)CH₂CH₂— Me Me Me Cl—CH₂CH₂C(═O)CH₂— Me Me Me Cl —CH₂C(═S)CH₂CH₂— Me Me Me Cl—CH₂CH₂C(═S)CH₂— Me Me Me Cl —CH₂C(═O)CH₂— Me Me Me Cl —CH₂C(═S)CH₂— MeMe Me Cl —CH(Me)— Me Me Me Cl —CH(OMe)— Me Me Me Cl —CH(Me)CH₂— Me Me MeCl —CH₂CH(Me)— Me Me Me Cl —CH₂CH(OMe)— Me Me Me Cl —CH(Me)CH₂CH₂— Me MeMe Cl —CH₂CH(Me)CH₂— Me Me Me Cl —CH₂CH₂CH(Me)— Me Me Me Cl —CH(Et)— MeMe Me Cl —CH(Et)CH₂— Me Me Me Cl —CH₂CH(Et)— Me Me Me Cl —CH(Et)CH₂CH₂—Me Me Me Cl —CH₂CH(Et)CH₂— Me Me Me Cl —CH₂CH₂CH(Et)— Me Me Me Cl—CH(OCF₃)— Me Me Me Cl —CH(CF₃)— Me Me Me Cl —CH₂CF₂CH₂— Me Me Me Cl—CH₂CHFCH₂— Me Me Me Cl —CH₂CF₂— Me Me Me Cl —CH₂CHF— Me Me Me Cl—CH(CN)— Me Me Me Cl V^(a) Me Me Me Cl V^(b) Me Me Me Cl V^(c) Me Me MeCl V^(d) Me Me Me Cl V^(e) Me Me Me Cl V^(f) Me Me Me Cl V^(g) Me Me MeCl V^(h) Me Me Me Cl —CH₂OC(═O)CH₂— Me Me Me Cl —CH₂C(═O)CH₂— Me Me MeCl —CH₂C(═O)— Me Me Me Cl —CH₂— Me Me Et Cl —CH₂CH₂— Me Me Et Cl—CH₂CH₂CH₂— Me Me Et Cl —CH₂CH₂CH₂CH₂— Me Me Et Cl —CH₂OCH₂CH₂— Me Me EtCl —CH₂CH₂OCH₂— Me Me Et Cl —CH₂C(═O)CH₂CH₂— Me Me Et Cl—CH₂CH₂C(═O)CH₂— Me Me Et Cl —CH₂C(═S)CH₂CH₂— Me Me Et Cl—CH₂CH₂C(═S)CH₂— Me Me Et Cl —CH₂C(═O)CH₂— Me Me Et Cl —CH₂C(═S)CH₂— MeMe Et Cl —CH(Me)— Me Me Et Cl —CH(OMe)— Me Me Et Cl —CH(Me)CH₂— Me Me EtCl —CH₂CH(Me)— Me Me Et Cl —CH₂CH(OMe)— Me Me Et Cl —CH(Me)CH₂CH₂— Me MeEt Cl —CH₂CH(Me)CH₂— Me Me Et Cl —CH₂CH₂CH(Me)— Me Me Et Cl —CH(Et)— MeMe Et Cl —CH(Et)CH₂— Me Me Et Cl —CH₂CH(Et)— Me Me Et Cl —CH(Et)CH₂CH₂—Me Me Et Cl —CH₂CH(Et)CH₂— Me Me Et Cl —CH₂CH₂CH(Et)— Me Me Et Cl—CH(OCF₃)— Me Me Et Cl —CH(CF₃)— Me Me Et Cl —CH₂CF₂CH₂— Me Me Et Cl—CH₂CHFCH₂— Me Me Et Cl —CH₂CF₂— Me Me Et Cl —CH₂CHF— Me Me Et Cl—CH(CN)— Me Me Et Cl V^(a) Me Me Et Cl V^(b) Me Me Et Cl V^(c) Me Me EtCl V^(d) Me Me Et Cl V^(e) Me Me Et Cl V^(f) Me Me Et Cl V^(g) Me Me EtCl V^(h) Me Me Et Cl —CH₂OC(═O)CH₂— Me Me Et Cl —CH₂C(═O)CH₂— Me Me EtCl —CH₂C(═O)— Me Me Et Cl —CH₂— Me Et Et Cl —CH₂CH₂— Me Et Et Cl—CH₂CH₂CH₂— Me Et Et Cl —CH₂CH₂CH₂CH₂— Me Et Et Cl —CH₂OCH₂CH₂— Me Et EtCl —CH₂CH₂OCH₂— Me Et Et Cl —CH₂C(═O)CH₂CH₂— Me Et Et Cl—CH₂CH₂C(═O)CH₂— Me Et Et Cl —CH₂C(═S)CH₂CH₂— Me Et Et Cl—CH₂CH₂C(═S)CH₂— Me Et Et Cl —CH₂C(═O)CH₂— Me Et Et Cl —CH₂C(═S)CH₂— MeEt Et Cl —CH(Me)— Me Et Et Cl —CH(OMe)— Me Et Et Cl —CH(Me)CH₂— Me Et EtCl —CH₂CH(Me)— Me Et Et Cl —CH₂CH(OMe)— Me Et Et Cl —CH(Me)CH₂CH₂— Me EtEt Cl —CH₂CH(Me)CH₂— Me Et Et Cl —CH₂CH₂CH(Me)— Me Et Et Cl —CH(Et)— MeEt Et Cl —CH(Et)CH₂— Me Et Et Cl —CH₂CH(Et)— Me Et Et Cl —CH(Et)CH₂CH₂—Me Et Et Cl —CH₂CH(Et)CH₂— Me Et Et Cl —CH₂CH₂CH(Et)— Me Et Et Cl—CH(OCF₃)— Me Et Et Cl —CH(CF₃)— Me Et Et Cl —CH₂CF₂CH₂— Me Et Et Cl—CH₂CHFCH₂— Me Et Et Cl —CH₂CF₂— Me Et Et Cl —CH₂CHF— Me Et Et Cl—CH(CN)— Me Et Et Cl V^(a) Me Et Et Cl V^(b) Me Et Et Cl V^(c) Me Et EtCl V^(d) Me Et Et Cl V^(e) Me Et Et Cl V^(f) Me Et Et Cl V^(g) Me Et EtCl V^(h) Me Et Et Cl —CH₂OC(═O)CH₂— Me Et Et Cl —CH₂C(═O)CH₂— Me Et EtCl —CH₂C(═O)— Me Et Et Cl —CH₂— Et Et Et Cl —CH₂CH₂— Et Et Et Cl—CH₂CH₂CH₂— Et Et Et Cl —CH₂CH₂CH₂CH₂— Et Et Et Cl —CH₂OCH₂CH₂— Et Et EtCl —CH₂CH₂OCH₂— Et Et Et Cl —CH₂C(═O)CH₂CH₂— Et Et Et Cl—CH₂CH₂C(═O)CH₂— Et Et Et Cl —CH₂C(═S)CH₂CH₂— Et Et Et Cl—CH₂CH₂C(═S)CH₂— Et Et Et Cl —CH₂C(═O)CH₂— Et Et Et Cl —CH₂C(═S)CH₂— EtEt Et Cl —CH(Me)— Et Et Et Cl —CH(OMe)— Et Et Et Cl —CH(Me)CH₂— Et Et EtCl —CH₂CH(Me)— Et Et Et Cl —CH₂CH(OMe)— Et Et Et Cl —CH(Me)CH₂CH₂— Et EtEt Cl —CH₂CH(Me)CH₂— Et Et Et Cl —CH₂CH₂CH(Me)— Et Et Et Cl —CH(Et)— EtEt Et Cl —CH(Et)CH₂— Et Et Et Cl —CH₂CH(Et)— Et Et Et Cl —CH(Et)CH₂CH₂—Et Et Et Cl —CH₂CH(Et)CH₂— Et Et Et Cl —CH₂CH₂CH(Et)— Et Et Et Cl—CH(OCF₃)— Et Et Et Cl —CH(CF₃)— Et Et Et Cl —CH₂CF₂CH₂— Et Et Et Cl—CH₂CHFCH₂— Et Et Et Cl —CH₂CF₂— Et Et Et Cl —CH₂CHF— Et Et Et Cl—CH(CN)— Et Et Et Cl V^(a) Et Et Et Cl V^(b) Et Et Et Cl V^(c) Et Et EtCl V^(d) Et Et Et Cl V^(e) Et Et Et Cl V^(f) Et Et Et Cl V^(g) Et Et EtCl V^(h) Et Et Et Cl —CH₂OC(═O)CH₂— Et Et Et Cl —CH₂C(═O)CH₂— Et Et EtCl —CH₂C(═O)— Et Et Et Cl —CH₂— Me Me i-Pr Cl —CH₂CH₂— Me Me i-Pr Cl—CH₂CH₂CH₂— Me Me i-Pr Cl —CH₂CH₂CH₂CH₂— Me Me i-Pr Cl —CH₂OCH₂CH₂— MeMe i-Pr Cl —CH₂CH₂OCH₂— Me Me i-Pr Cl —CH₂C(═O)CH₂CH₂— Me Me i-Pr Cl—CH₂CH₂C(═O)CH₂— Me Me i-Pr Cl —CH₂C(═S)CH₂CH₂— Me Me i-Pr Cl—CH₂CH₂C(═S)CH₂— Me Me i-Pr Cl —CH₂C(═O)CH₂— Me Me i-Pr Cl —CH₂C(═S)CH₂—Me Me i-Pr Cl —CH(Me)— Me Me i-Pr Cl —CH(OMe)— Me Me i-Pr Cl —CH(Me)CH₂—Me Me i-Pr Cl —CH₂CH(Me)— Me Me i-Pr Cl —CH₂CH(OMe)— Me Me i-Pr Cl—CH(Me)CH₂CH₂— Me Me i-Pr Cl —CH₂CH(Me)CH₂— Me Me i-Pr Cl —CH₂CH₂CH(Me)—Me Me i-Pr Cl —CH(Et)— Me Me i-Pr Cl —CH(Et)CH₂— Me Me i-Pr Cl—CH₂CH(Et)— Me Me i-Pr Cl —CH(Et)CH₂CH₂— Me Me i-Pr Cl —CH₂CH(Et)CH₂— MeMe i-Pr Cl —CH₂CH₂CH(Et)— Me Me i-Pr Cl —CH(OCF₃)— Me Me i-Pr Cl—CH(CF₃)— Me Me i-Pr Cl —CH₂CF₂CH₂— Me Me i-Pr Cl —CH₂CHFCH₂— Me Me i-PrCl —CH₂CF₂— Me Me i-Pr Cl —CH₂CHF— Me Me i-Pr Cl —CH(CN)— Me Me i-Pr ClV^(a) Me Me i-Pr Cl V^(b) Me Me i-Pr Cl V^(c) Me Me i-Pr Cl V^(d) Me Mei-Pr Cl V^(e) Me Me i-Pr Cl V^(f) Me Me i-Pr Cl V^(g) Me Me i-Pr ClV^(h) Me Me i-Pr Cl —CH₂OC(═O)CH₂— Me Me i-Pr Cl —CH₂C(═O)CH₂— Me Mei-Pr Cl —CH₂C(═O)— Me Me i-Pr Cl —CH₂— Me Et i-Pr Cl —CH₂CH₂— Me Et i-PrCl —CH₂CH₂CH₂— Me Et i-Pr Cl —CH₂CH₂CH₂CH₂— Me Et i-Pr Cl —CH₂OCH₂CH₂—Me Et i-Pr Cl —CH₂CH₂OCH₂— Me Et i-Pr Cl —CH₂C(═O)CH₂CH₂— Me Et i-Pr Cl—CH₂CH₂C(═O)CH₂— Me Et i-Pr Cl —CH₂C(═S)CH₂CH₂— Me Et i-Pr Cl—CH₂CH₂C(═S)CH₂— Me Et i-Pr Cl —CH₂C(═O)CH₂— Me Et i-Pr Cl —CH₂C(═S)CH₂—Me Et i-Pr Cl —CH(Me)— Me Et i-Pr Cl —CH(OMe)— Me Et i-Pr Cl —CH(Me)CH₂—Me Et i-Pr Cl —CH₂CH(Me)— Me Et i-Pr Cl —CH₂CH(OMe)— Me Et i-Pr Cl—CH(Me)CH₂CH₂— Me Et i-Pr Cl —CH₂CH(Me)CH₂— Me Et i-Pr Cl —CH₂CH₂CH(Me)—Me Et i-Pr Cl —CH(Et)— Me Et i-Pr Cl —CH(Et)CH₂— Me Et i-Pr Cl—CH₂CH(Et)— Me Et i-Pr Cl —CH(Et)CH₂CH₂— Me Et i-Pr Cl —CH₂CH(Et)CH₂— MeEt i-Pr Cl —CH₂CH₂CH(Et)— Me Et i-Pr Cl —CH(OCF₃)— Me Et i-Pr Cl—CH(CF₃)— Me Et i-Pr Cl —CH₂CF₂CH₂— Me Et i-Pr Cl —CH₂CHFCH₂— Me Et i-PrCl —CH₂CF₂— Me Et i-Pr Cl —CH₂CHF— Me Et i-Pr Cl —CH(CN)— Me Et i-Pr ClV^(a) Me Et i-Pr Cl V^(b) Me Et i-Pr Cl V^(c) Me Et i-Pr Cl V^(d) Me Eti-Pr Cl V^(e) Me Et i-Pr Cl V^(f) Me Et i-Pr Cl V^(g) Me Et i-Pr ClV^(h) Me Et i-Pr Cl —CH₂OC(═O)CH₂— Me Et i-Pr Cl —CH₂C(═O)CH₂— Me Eti-Pr Cl —CH₂C(═O)— Me Et i-Pr Cl —CH₂— Me Me Ph Cl —CH₂CH₂— Me Me Ph Cl—CH₂CH₂CH₂— Me Me Ph Cl —CH₂CH₂CH₂CH₂— Me Me Ph Cl —CH₂OCH₂CH₂— Me Me PhCl —CH₂CH₂OCH₂— Me Me Ph Cl —CH₂C(═O)CH₂CH₂— Me Me Ph Cl—CH₂CH₂C(═O)CH₂— Me Me Ph Cl —CH₂C(═S)CH₂CH₂— Me Me Ph Cl—CH₂CH₂C(═S)CH₂— Me Me Ph Cl —CH₂C(═O)CH₂— Me Me Ph Cl —CH₂C(═S)CH₂— MeMe Ph Cl —CH(Me)— Me Me Ph Cl —CH(OMe)— Me Me Ph Cl —CH(Me)CH₂— Me Me PhCl —CH₂CH(Me)— Me Me Ph Cl —CH₂CH(OMe)— Me Me Ph Cl —CH(Me)CH₂CH₂— Me MePh Cl —CH₂CH(Me)CH₂— Me Me Ph Cl —CH₂CH₂CH(Me)— Me Me Ph Cl —CH(Et)— MeMe Ph Cl —CH(Et)CH₂— Me Me Ph Cl —CH₂CH(Et)— Me Me Ph Cl —CH(Et)CH₂CH₂—Me Me Ph Cl —CH₂CH(Et)CH₂— Me Me Ph Cl —CH₂CH₂CH(Et)— Me Me Ph Cl—CH(OCF₃)— Me Me Ph Cl —CH(CF₃)— Me Me Ph Cl —CH₂CF₂CH₂— Me Me Ph Cl—CH₂CHFCH₂— Me Me Ph Cl —CH₂CF₂— Me Me Ph Cl —CH₂CHF— Me Me Ph Cl—CH(CN)— Me Me Ph Cl V^(a) Me Me Ph Cl V^(b) Me Me Ph Cl V^(c) Me Me PhCl V^(d) Me Me Ph Cl V^(e) Me Me Ph Cl V^(f) Me Me Ph Cl V^(g) Me Me PhCl V^(h) Me Me Ph Cl —CH₂OC(═O)CH₂— Me Me Ph Cl —CH₂C(═O)CH₂— Me Me PhCl —CH₂C(═O)— Me Me Ph Cl —CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂— Me Me 4-Cl—PhCl —CH₂CH₂CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂CH₂CH₂— Me Me 4-Cl—Ph Cl—CH₂OCH₂CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂OCH₂— Me Me 4-Cl—Ph Cl—CH₂C(═O)CH₂CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂C(═O)CH₂— Me Me 4-Cl—Ph Cl—CH₂C(═S)CH₂CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂C(═S)CH₂— Me Me 4-Cl—Ph Cl—CH₂C(═O)CH₂— Me Me 4-Cl—Ph Cl —CH₂C(═S)CH₂— Me Me 4-Cl—Ph Cl —CH(Me)—Me Me 4-Cl—Ph Cl —CH(OMe)— Me Me 4-Cl—Ph Cl —CH(Me)CH₂— Me Me 4-Cl—Ph Cl—CH₂CH(Me)— Me Me 4-Cl—Ph Cl —CH₂CH(OMe)— Me Me 4-Cl—Ph Cl—CH(Me)CH₂CH₂— Me Me 4-Cl—Ph Cl —CH₂CH(Me)CH₂— Me Me 4-Cl—Ph Cl—CH₂CH₂CH(Me)— Me Me 4-Cl—Ph Cl —CH(Et)— Me Me 4-Cl—Ph Cl —CH(Et)CH₂— MeMe 4-Cl—Ph Cl —CH₂CH(Et)— Me Me 4-Cl—Ph Cl —CH(Et)CH₂CH₂— Me Me 4-Cl—PhCl —CH₂CH(Et)CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂CH(Et)— Me Me 4-Cl—Ph Cl—CH(OCF₃)— Me Me 4-Cl—Ph Cl —CH(CF₃)— Me Me 4-Cl—Ph Cl —CH₂CF₂CH₂— Me Me4-Cl—Ph Cl —CH₂CHFCH₂— Me Me 4-Cl—Ph Cl —CH₂CF₂— Me Me 4-Cl—Ph Cl—CH₂CHF— Me Me 4-Cl—Ph Cl —CH(CN)— Me Me 4-Cl—Ph Cl V^(a) Me Me 4-Cl—PhCl V^(b) Me Me 4-Cl—Ph Cl V^(c) Me Me 4-Cl—Ph Cl V^(d) Me Me 4-Cl—Ph ClV^(e) Me Me 4-Cl—Ph Cl V^(f) Me Me 4-Cl—Ph Cl V^(g) Me Me 4-Cl—Ph ClV^(h) Me Me 4-Cl—Ph Cl —CH₂OC(═O)CH₂— Me Me 4-Cl—Ph Cl —CH₂C(═O)CH₂— MeMe 4-Cl—Ph Cl —CH₂C(═O)— Me Me 4-Cl—Ph Cl —CH₂— Me Me 3-Cl—Ph Cl—CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂CH₂CH₂— MeMe 3-Cl—Ph Cl —CH₂OCH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂OCH₂— Me Me 3-Cl—PhCl —CH₂C(═O)CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂C(═O)CH₂— Me Me 3-Cl—Ph Cl—CH₂C(═S)CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂C(═S)CH₂— Me Me 3-Cl—Ph Cl—CH₂C(═O)CH₂— Me Me 3-Cl—Ph Cl —CH₂C(═S)CH₂— Me Me 3-Cl—Ph Cl —CH(Me)—Me Me 3-Cl—Ph Cl —CH(OMe)— Me Me 3-Cl—Ph Cl —CH(Me)CH₂— Me Me 3-Cl—Ph Cl—CH₂CH(Me)— Me Me 3-Cl—Ph Cl —CH₂CH(OMe)— Me Me 3-Cl—Ph Cl—CH(Me)CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH(Me)CH₂— Me Me 3-Cl—Ph Cl—CH₂CH₂CH(Me)— Me Me 3-Cl—Ph Cl —CH(Et)— Me Me 3-Cl—Ph Cl —CH(Et)CH₂— MeMe 3-Cl—Ph Cl —CH₂CH(Et)— Me Me 3-Cl—Ph Cl —CH(Et)CH₂CH₂— Me Me 3-Cl—PhCl —CH₂CH(Et)CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂CH(Et)— Me Me 3-Cl—Ph Cl—CH(OCF₃)— Me Me 3-Cl—Ph Cl —CH(CF₃)— Me Me 3-Cl—Ph Cl —CH₂CF₂CH₂— Me Me3-Cl—Ph Cl —CH₂CHFCH₂— Me Me 3-Cl—Ph Cl —CH₂CF₂— Me Me 3-Cl—Ph Cl—CH₂CHF— Me Me 3-Cl—Ph Cl —CH(CN)— Me Me 3-Cl—Ph Cl V^(a) Me Me 3-Cl—PhCl V^(b) Me Me 3-Cl—Ph Cl V^(c) Me Me 3-Cl—Ph Cl V^(d) Me Me 3-Cl—Ph ClV^(e) Me Me 3-Cl—Ph Cl V^(f) Me Me 3-Cl—Ph Cl V^(g) Me Me 3-Cl—Ph ClV^(h) Me Me 3-Cl—Ph Cl —CH₂OC(═O)CH₂— Me Me 3-Cl—Ph Cl —CH₂C(═O)CH₂— MeMe 3-Cl—Ph Cl —CH₂C(═O)— Me Me 3-Cl—Ph Cl —CH₂— Me Me 2-Cl—Ph Cl—CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂CH₂CH₂— MeMe 2-Cl—Ph Cl —CH₂OCH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂OCH₂— Me Me 2-Cl—PhCl —CH₂C(═O)CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂C(═O)CH₂— Me Me 2-Cl—Ph Cl—CH₂C(═S)CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂C(═S)CH₂— Me Me 2-Cl—Ph Cl—CH₂C(═O)CH₂— Me Me 2-Cl—Ph Cl —CH₂C(═S)CH₂— Me Me 2-Cl—Ph Cl —CH(Me)—Me Me 2-Cl—Ph Cl —CH(OMe)— Me Me 2-Cl—Ph Cl —CH(Me)CH₂— Me Me 2-Cl—Ph Cl—CH₂CH(Me)— Me Me 2-Cl—Ph Cl —CH₂CH(OMe)— Me Me 2-Cl—Ph Cl—CH(Me)CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH(Me)CH₂— Me Me 2-Cl—Ph Cl—CH₂CH₂CH(Me)— Me Me 2-Cl—Ph Cl —CH(Et)— Me Me 2-Cl—Ph Cl —CH(Et)CH₂— MeMe 2-Cl—Ph Cl —CH₂CH(Et)— Me Me 2-Cl—Ph Cl —CH(Et)CH₂CH₂— Me Me 2-Cl—PhCl —CH₂CH(Et)CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂CH(Et)— Me Me 2-Cl—Ph Cl—CH(OCF₃)— Me Me 2-Cl—Ph Cl —CH(CF₃)— Me Me 2-Cl—Ph Cl —CH₂CF₂CH₂— Me Me2-Cl—Ph Cl —CH₂CHFCH₂— Me Me 2-Cl—Ph Cl —CH₂CF₂— Me Me 2-Cl—Ph Cl—CH₂CHF— Me Me 2-Cl—Ph Cl —CH(CN)— Me Me 2-Cl—Ph Cl V^(a) Me Me 2-Cl—PhCl V^(b) Me Me 2-Cl—Ph Cl V^(c) Me Me 2-Cl—Ph Cl V^(d) Me Me 2-Cl—Ph ClV^(e) Me Me 2-Cl—Ph Cl V^(f) Me Me 2-Cl—Ph Cl V^(g) Me Me 2-Cl—Ph ClV^(h) Me Me 2-Cl—Ph Cl —CH₂OC(═O)CH₂— Me Me 2-Cl—Ph Cl —CH₂C(═O)CH₂— MeMe 2-Cl—Ph Cl —CH₂C(═O)— Me Me 2-Cl—Ph Cl —CH₂— Me Me c-Pr Cl —CH₂CH₂—Me Me c-Pr Cl —CH₂CH₂CH₂— Me Me c-Pr Cl —CH₂CH₂CH₂CH₂— Me Me c-Pr Cl—CH₂OCH₂CH₂— Me Me c-Pr Cl —CH₂CH₂OCH₂— Me Me c-Pr Cl —CH₂C(═O)CH₂CH₂—Me Me c-Pr Cl —CH₂CH₂C(═O)CH₂— Me Me c-Pr Cl —CH₂C(═S)CH₂CH₂— Me Me c-PrCl —CH₂CH₂C(═S)CH₂— Me Me c-Pr Cl —CH₂C(═O)CH₂— Me Me c-Pr Cl—CH₂C(═S)CH₂— Me Me c-Pr Cl —CH(Me)— Me Me c-Pr Cl —CH(OMe)— Me Me c-PrCl —CH(Me)CH₂— Me Me c-Pr Cl —CH₂CH(Me)— Me Me c-Pr Cl —CH₂CH(OMe)— MeMe c-Pr Cl —CH(Me)CH₂CH₂— Me Me c-Pr Cl —CH₂CH(Me)CH₂— Me Me c-Pr Cl—CH₂CH₂CH(Me)— Me Me c-Pr Cl —CH(Et)— Me Me c-Pr Cl —CH(Et)CH₂— Me Mec-Pr Cl —CH₂CH(Et)— Me Me c-Pr Cl —CH(Et)CH₂CH₂— Me Me c-Pr Cl—CH₂CH(Et)CH₂— Me Me c-Pr Cl —CH₂CH₂CH(Et)— Me Me c-Pr Cl —CH(OCF₃)— MeMe c-Pr Cl —CH(CF₃)— Me Me c-Pr Cl —CH₂CF₂CH₂— Me Me c-Pr Cl —CH₂CHFCH₂—Me Me c-Pr Cl —CH₂CF₂— Me Me c-Pr Cl —CH₂CHF— Me Me c-Pr Cl —CH(CN)— MeMe c-Pr Cl V^(a) Me Me c-Pr Cl V^(b) Me Me c-Pr Cl V^(c) Me Me c-Pr ClV^(d) Me Me c-Pr Cl V^(e) Me Me c-Pr Cl V^(f) Me Me c-Pr Cl V^(g) Me Mec-Pr Cl V^(h) Me Me c-Pr Cl —CH₂OC(═O)CH₂— Me Me c-Pr Cl —CH₂C(═O)CH₂—Me Me c-Pr Cl —CH₂C(═O)— Me Me c-Pr Me —CH₂— Me Me Me Me —CH₂CH₂— Me MeMe Me —CH₂CH₂CH₂— Me Me Me Me —CH₂CH₂CH₂CH₂— Me Me Me Me —CH₂OCH₂CH₂— MeMe Me Me —CH₂CH₂OCH₂— Me Me Me Me —CH₂C(═O)CH₂CH₂— Me Me Me Me—CH₂CH₂C(═O)CH₂— Me Me Me Me —CH₂C(═S)CH₂CH₂— Me Me Me Me—CH₂CH₂C(═S)CH₂— Me Me Me Me —CH₂C(═O)CH₂— Me Me Me Me —CH₂C(═S)CH₂— MeMe Me Me —CH(Me)— Me Me Me Me —CH(OMe)— Me Me Me Me —CH(Me)CH₂— Me Me MeMe —CH₂CH(Me)— Me Me Me Me —CH₂CH(OMe)— Me Me Me Me —CH(Me)CH₂CH₂— Me MeMe Me —CH₂CH(Me)CH₂— Me Me Me Me —CH₂CH₂CH(Me)— Me Me Me Me —CH(Et)— MeMe Me Me —CH(Et)CH₂— Me Me Me Me —CH₂CH(Et)— Me Me Me Me —CH(Et)CH₂CH₂—Me Me Me Me —CH₂CH(Et)CH₂— Me Me Me Me —CH₂CH₂CH(Et)— Me Me Me Me—CH(OCF₃)— Me Me Me Me —CH(CF₃)— Me Me Me Me —CH₂CF₂CH₂— Me Me Me Me—CH₂CHFCH₂— Me Me Me Me —CH₂CF₂— Me Me Me Me —CH₂CHF— Me Me Me Me—CH(CN)— Me Me Me Me V^(a) Me Me Me Me V^(b) Me Me Me Me V^(c) Me Me MeMe V^(d) Me Me Me Me V^(e) Me Me Me Me V^(f) Me Me Me Me V^(g) Me Me MeMe V^(h) Me Me Me Me —CH₂OC(═O)CH₂— Me Me Me Me —CH₂C(═O)CH₂— Me Me MeMe —CH₂C(═O)— Me Me Me Me —CH₂— Me Et Et Me —CH₂CH₂— Me Et Et Me—CH₂CH₂CH₂— Me Et Et Me —CH₂CH₂CH₂CH₂— Me Et Et Me —CH₂OCH₂CH₂— Me Et EtMe —CH₂CH₂OCH₂— Me Et Et Me —CH₂C(═O)CH₂CH₂— Me Et Et Me—CH₂CH₂C(═O)CH₂— Me Et Et Me —CH₂C(═S)CH₂CH₂— Me Et Et Me—CH₂CH₂C(═S)CH₂— Me Et Et Me —CH₂C(═O)CH₂— Me Et Et Me —CH₂C(═S)CH₂— MeEt Et Me —CH(Me)— Me Et Et Me —CH(OMe)— Me Et Et Me —CH(Me)CH₂— Me Et EtMe —CH₂CH(Me)— Me Et Et Me —CH₂CH(OMe)— Me Et Et Me —CH(Me)CH₂CH₂— Me EtEt Me —CH₂CH(Me)CH₂— Me Et Et Me —CH₂CH₂CH(Me)— Me Et Et Me —CH(Et)— MeEt Et Me —CH(Et)CH₂— Me Et Et Me —CH₂CH(Et)— Me Et Et Me —CH(Et)CH₂CH₂—Me Et Et Me —CH₂CH(Et)CH₂— Me Et Et Me —CH₂CH₂CH(Et)— Me Et Et Me—CH(OCF₃)— Me Et Et Me —CH(CF₃)— Me Et Et Me —CH₂CF₂CH₂— Me Et Et Me—CH₂CHFCH₂— Me Et Et Me —CH₂CF₂— Me Et Et Me —CH₂CHF— Me Et Et Me—CH(CN)— Me Et Et Me V^(a) Me Et Et Me V^(b) Me Et Et Me V^(c) Me Et EtMe 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Me i-Pr F —CH₂C(═O)CH₂—Me Me i-Pr F —CH₂C(═O)— Me Me i-Pr F —CH₂— Me Et i-Pr F —CH₂CH₂— Me Eti-Pr F —CH₂CH₂CH₂— Me Et i-Pr F —CH₂CH₂CH₂CH₂— Me Et i-Pr F —CH₂OCH₂CH₂—Me Et i-Pr F —CH₂CH₂OCH₂— Me Et i-Pr F —CH₂C(═O)CH₂CH₂— Me Et i-Pr F—CH₂CH₂C(═O)CH₂— Me Et i-Pr F —CH₂C(═S)CH₂CH₂— Me Et i-Pr F—CH₂CH₂C(═S)CH₂— Me Et i-Pr F —CH₂C(═O)CH₂— Me Et i-Pr F —CH₂C(═S)CH₂—Me Et i-Pr F —CH(Me)— Me Et i-Pr F —CH(OMe)— Me Et i-Pr F —CH(Me)CH₂— MeEt i-Pr F —CH₂CH(Me)— Me Et i-Pr F —CH₂CH(OMe)— Me Et i-Pr F—CH(Me)CH₂CH₂— Me Et i-Pr F —CH₂CH(Me)CH₂— Me Et i-Pr F —CH₂CH₂CH(Me)—Me Et i-Pr F —CH(Et)— Me Et i-Pr F —CH(Et)CH₂— Me Et i-Pr F —CH₂CH(Et)—Me Et i-Pr F —CH(Et)CH₂CH₂— Me Et i-Pr F —CH₂CH(Et)CH₂— Me Et i-Pr F—CH₂CH₂CH(Et)— Me Et i-Pr F —CH(OCF₃)— Me Et i-Pr F —CH(CF₃)— Me Et i-PrF —CH₂CF₂CH₂— Me Et i-Pr F —CH₂CHFCH₂— Me Et i-Pr F —CH₂CF₂— Me Et i-PrF —CH₂CHF— Me Et i-Pr F —CH(CN)— Me Et i-Pr F V^(a) Me Et i-Pr F V^(b)Me Et i-Pr F V^(c) Me Et i-Pr F V^(d) Me Et i-Pr F V^(e) Me Et i-Pr FV^(f) Me Et i-Pr F V^(g) Me Et i-Pr F V^(h) Me Et i-Pr F —CH₂OC(═O)CH₂—Me Et i-Pr F —CH₂C(═O)CH₂— Me Et i-Pr F —CH₂C(═O)— Me Et i-Pr F —CH₂— MeMe Ph F —CH₂CH₂— Me Me Ph F —CH₂CH₂CH₂— Me Me Ph F —CH₂CH₂CH₂CH₂— Me MePh F —CH₂OCH₂CH₂— Me Me Ph F —CH₂CH₂OCH₂— Me Me Ph F —CH₂C(═O)CH₂CH₂— MeMe Ph F —CH₂CH₂C(═O)CH₂— Me Me Ph F —CH₂C(═S)CH₂CH₂— Me Me Ph F—CH₂CH₂C(═S)CH₂— Me Me Ph F —CH₂C(═O)CH₂— Me Me Ph F —CH₂C(═S)CH₂— Me MePh F —CH(Me)— Me Me Ph F —CH(OMe)— Me Me Ph F —CH(Me)CH₂— Me Me Ph F—CH₂CH(Me)— Me Me Ph F —CH₂CH(OMe)— Me Me Ph F —CH(Me)CH₂CH₂— Me Me Ph F—CH₂CH(Me)CH₂— Me Me Ph F —CH₂CH₂CH(Me)— Me Me Ph F —CH(Et)— Me Me Ph F—CH(Et)CH₂— Me Me Ph F —CH₂CH(Et)— Me Me Ph F —CH(Et)CH₂CH₂— Me Me Ph F—CH₂CH(Et)CH₂— Me Me Ph F —CH₂CH₂CH(Et)— Me Me Ph F —CH(OCF₃)— Me Me PhF —CH(CF₃)— Me Me Ph F —CH₂CF₂CH₂— Me Me Ph F —CH₂CHFCH₂— Me Me Ph F—CH₂CF₂— Me Me Ph F —CH₂CHF— Me Me Ph F —CH(CN)— Me Me Ph F V^(a) Me MePh F V^(b) Me Me Ph F V^(c) Me Me Ph F V^(d) Me Me Ph F V^(e) Me Me Ph FV^(f) Me Me Ph F V^(g) Me Me Ph F V^(h) Me Me Ph F —CH₂OC(═O)CH₂— Me MePh F —CH₂C(═O)CH₂— Me Me Ph F —CH₂C(═O)— Me Me Ph F —CH₂— Me Me 4-Cl—PhF —CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH₂CH₂— MeMe 4-Cl—Ph F —CH₂OCH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂OCH₂— Me Me 4-Cl—Ph F—CH₂C(═O)CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂C(═O)CH₂— Me Me 4-Cl—Ph F—CH₂C(═S)CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂C(═S)CH₂— Me Me 4-Cl—Ph F—CH₂C(═O)CH₂— Me Me 4-Cl—Ph F —CH₂C(═S)CH₂— Me Me 4-Cl—Ph F —CH(Me)— MeMe 4-Cl—Ph F —CH(OMe)— Me Me 4-Cl—Ph F —CH(Me)CH₂— Me Me 4-Cl—Ph F—CH₂CH(Me)— Me Me 4-Cl—Ph F —CH₂CH(OMe)— Me Me 4-Cl—Ph F —CH(Me)CH₂CH₂—Me Me 4-Cl—Ph F —CH₂CH(Me)CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH(Me)— Me Me4-Cl—Ph F —CH(Et)— Me Me 4-Cl—Ph F —CH(Et)CH₂— Me Me 4-Cl—Ph F—CH₂CH(Et)— Me Me 4-Cl—Ph F —CH(Et)CH₂CH₂— Me Me 4-Cl—Ph F—CH₂CH(Et)CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH(Et)— Me Me 4-Cl—Ph F —CH(OCF₃)—Me Me 4-Cl—Ph F —CH(CF₃)— Me Me 4-Cl—Ph F —CH₂CF₂CH₂— Me Me 4-Cl—Ph F—CH₂CHFCH₂— Me Me 4-Cl—Ph F —CH₂CF₂— Me Me 4-Cl—Ph F —CH₂CHF— Me Me4-Cl—Ph F —CH(CN)— Me Me 4-Cl—Ph F V^(a) Me Me 4-Cl—Ph F V^(b) Me Me4-Cl—Ph F V^(c) Me Me 4-Cl—Ph F V^(d) Me Me 4-Cl—Ph F V^(e) Me Me4-Cl—Ph F V^(f) Me Me 4-Cl—Ph F V^(g) Me Me 4-Cl—Ph F V^(h) Me Me4-Cl—Ph F —CH₂OC(═O)CH₂— Me Me 4-Cl—Ph F —CH₂C(═O)CH₂— Me Me 4-Cl—Ph F—CH₂C(═O)— Me Me 4-Cl—Ph F —CH₂— Me Me 3-Cl—Ph F —CH₂CH₂— Me Me 3-Cl—PhF —CH₂CH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂CH₂CH₂— Me Me 3-Cl—Ph F—CH₂OCH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂OCH₂— Me Me 3-Cl—Ph F—CH₂C(═O)CH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂C(═O)CH₂— Me Me 3-Cl—Ph F—CH₂C(═S)CH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂C(═S)CH₂— Me Me 3-Cl—Ph F—CH₂C(═O)CH₂— Me Me 3-Cl—Ph F —CH₂C(═S)CH₂— Me Me 3-Cl—Ph F —CH(Me)— MeMe 3-Cl—Ph F —CH(OMe)— Me Me 3-Cl—Ph F —CH(Me)CH₂— Me Me 3-Cl—Ph F—CH₂CH(Me)— Me Me 3-Cl—Ph F —CH₂CH(OMe)— Me Me 3-Cl—Ph F —CH(Me)CH₂CH₂—Me Me 3-Cl—Ph F —CH₂CH(Me)CH₂— Me Me 3-Cl—Ph F —CH₂CH₂CH(Me)— Me Me3-Cl—Ph F —CH(Et)— Me Me 3-Cl—Ph F —CH(Et)CH₂— Me Me 3-Cl—Ph F—CH₂CH(Et)— Me Me 3-Cl—Ph F —CH(Et)CH₂CH₂— Me Me 3-Cl—Ph F—CH₂CH(Et)CH₂— Me Me 3-Cl—Ph F —CH₂CH₂CH(Et)— Me Me 3-Cl—Ph F —CH(OCF₃)—Me Me 3-Cl—Ph F —CH(CF₃)— Me Me 3-Cl—Ph F —CH₂CF₂CH₂— Me Me 3-Cl—Ph F—CH₂CHFCH₂— Me Me 3-Cl—Ph F —CH₂CF₂— Me Me 3-Cl—Ph F —CH₂CHF— Me Me3-Cl—Ph F —CH(CN)— Me Me 3-Cl—Ph F V^(a) Me Me 3-Cl—Ph F V^(b) Me Me3-Cl—Ph F V^(c) Me Me 3-Cl—Ph F V^(d) Me Me 3-Cl—Ph F V^(e) Me Me3-Cl—Ph F V^(f) Me Me 3-Cl—Ph F V^(g) Me Me 3-Cl—Ph F V^(h) Me Me3-Cl—Ph F —CH₂OC(═O)CH₂— Me Me 3-Cl—Ph F —CH₂C(═O)CH₂— Me Me 3-Cl—Ph F—CH₂C(═O)— Me Me 3-Cl—Ph F —CH₂— Me Me 2-Cl—Ph F —CH₂CH₂— Me Me 2-Cl—PhF —CH₂CH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂CH₂CH₂— Me Me 2-Cl—Ph F—CH₂OCH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂OCH₂— Me Me 2-Cl—Ph F—CH₂C(═O)CH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂C(═O)CH₂— Me Me 2-Cl—Ph F—CH₂C(═S)CH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂C(═S)CH₂— Me Me 2-Cl—Ph F—CH₂C(═O)CH₂— Me Me 2-Cl—Ph F —CH₂C(═S)CH₂— Me Me 2-Cl—Ph F —CH(Me)— MeMe 2-Cl—Ph F —CH(OMe)— Me Me 2-Cl—Ph F —CH(Me)CH₂— Me Me 2-Cl—Ph F—CH₂CH(Me)— Me Me 2-Cl—Ph F —CH₂CH(OMe)— Me Me 2-Cl—Ph F —CH(Me)CH₂CH₂—Me Me 2-Cl—Ph F —CH₂CH(Me)CH₂— Me Me 2-Cl—Ph F —CH₂CH₂CH(Me)— Me Me2-Cl—Ph F —CH(Et)— Me Me 2-Cl—Ph F —CH(Et)CH₂— Me Me 2-Cl—Ph F—CH₂CH(Et)— Me Me 2-Cl—Ph F —CH(Et)CH₂CH₂— Me Me 2-Cl—Ph F—CH₂CH(Et)CH₂— Me Me 2-Cl—Ph F —CH₂CH₂CH(Et)— Me Me 2-Cl—Ph F —CH(OCF₃)—Me Me 2-Cl—Ph F —CH(CF₃)— Me Me 2-Cl—Ph F —CH₂CF₂CH₂— Me Me 2-Cl—Ph F—CH₂CHFCH₂— Me Me 2-Cl—Ph F —CH₂CF₂— Me Me 2-Cl—Ph F —CH₂CHF— Me Me2-Cl—Ph F —CH(CN)— Me Me 2-Cl—Ph F V^(a) Me Me 2-Cl—Ph F V^(b) Me Me2-Cl—Ph F V^(c) Me Me 2-Cl—Ph F V^(d) Me Me 2-Cl—Ph F V^(e) Me Me2-Cl—Ph F V^(f) Me Me 2-Cl—Ph F V^(g) Me Me 2-Cl—Ph F V^(h) Me Me2-Cl—Ph F —CH₂OC(═O)CH₂— Me Me 2-Cl—Ph F —CH₂C(═O)CH₂— Me Me 2-Cl—Ph F—CH₂C(═O)— Me Me 2-Cl—Ph F —CH₂— Me Me c-Pr F —CH₂CH₂— Me Me c-Pr F—CH₂CH₂CH₂— Me Me c-Pr F —CH₂CH₂CH₂CH₂— Me Me c-Pr F —CH₂OCH₂CH₂— Me Mec-Pr F —CH₂CH₂OCH₂— Me Me c-Pr F —CH₂C(═O)CH₂CH₂— Me Me c-Pr F—CH₂CH₂C(═O)CH₂— Me Me c-Pr F —CH₂C(═S)CH₂CH₂— Me Me c-Pr F—CH₂CH₂C(═S)CH₂— Me Me c-Pr F —CH₂C(═O)CH₂— Me Me c-Pr F —CH₂C(═S)CH₂—Me Me c-Pr F —CH(Me)— Me Me c-Pr F —CH(OMe)— Me Me c-Pr F —CH(Me)CH₂— MeMe c-Pr F —CH₂CH(Me)— Me Me c-Pr F —CH₂CH(OMe)— Me Me c-Pr F—CH(Me)CH₂CH₂— Me Me c-Pr F —CH₂CH(Me)CH₂— Me Me c-Pr F —CH₂CH₂CH(Me)—Me Me c-Pr F —CH(Et)— Me Me c-Pr F —CH(Et)CH₂— Me Me c-Pr F —CH₂CH(Et)—Me Me c-Pr F —CH(Et)CH₂CH₂— Me Me c-Pr F —CH₂CH(Et)CH₂— Me Me c-Pr F—CH₂CH₂CH(Et)— Me Me c-Pr F —CH(OCF₃)— Me Me c-Pr F —CH(CF₃)— Me Me c-PrF —CH₂CF₂CH₂— Me Me c-Pr F —CH₂CHFCH₂— Me Me c-Pr F —CH₂CF₂— Me Me c-PrF —CH₂CHF— Me Me c-Pr F —CH(CN)— Me Me c-Pr F V^(a) Me Me c-Pr F V^(b)Me Me c-Pr F V^(c) Me Me c-Pr F V^(d) Me Me c-Pr F V^(e) Me Me c-Pr FV^(f) Me Me c-Pr F V^(g) Me Me c-Pr F V^(h) Me Me c-Pr F —CH₂OC(═O)CH₂—Me Me c-Pr F —CH₂C(═O)CH₂— Me Me c-Pr F —CH₂C(═O)— Me Me c-Pr Me —CH₂—Me Me Et Me —CH₂CH₂— Me Me Et Me —CH₂CH₂CH₂— Me Me Et Me —CH₂CH₂CH₂CH₂—Me Me Et Me —CH₂OCH₂CH₂— Me Me Et Me —CH₂CH₂OCH₂— Me Me Et Me—CH₂C(═O)CH₂CH₂— Me Me Et Me —CH₂CH₂C(═O)CH₂— Me Me Et Me—CH₂C(═S)CH₂CH₂— Me Me Et Me —CH₂CH₂C(═S)CH₂— Me Me Et Me —CH₂C(═O)CH₂—Me Me Et Me —CH₂C(═S)CH₂— Me Me Et Me —CH(Me)— Me Me Et Me —CH(OMe)— MeMe Et Me —CH(Me)CH₂— Me Me Et Me —CH₂CH(Me)— Me Me Et Me —CH₂CH(OMe)— MeMe Et Me —CH(Me)CH₂CH₂— Me Me Et Me —CH₂CH(Me)CH₂— Me Me Et Me—CH₂CH₂CH(Me)— Me Me Et Me —CH(Et)— Me Me Et Me —CH(Et)CH₂— Me Me Et Me—CH₂CH(Et)— Me Me Et Me —CH(Et)CH₂CH₂— Me Me Et Me —CH₂CH(Et)CH₂— Me MeEt Me —CH₂CH₂CH(Et)— Me Me Et Me —CH(OCF₃)— Me Me Et Me —CH(CF₃)— Me MeEt Me —CH₂CF₂CH₂— Me Me Et Me —CH₂CHFCH₂— Me Me Et Me —CH₂CF₂— Me Me EtMe —CH₂CHF— Me Me Et Me —CH(CN)— Me Me Et Me V^(a) Me Me Et Me V^(b) MeMe Et Me V^(c) Me Me Et Me V^(d) Me Me Et Me V^(e) Me Me Et Me V^(f) MeMe Et Me V^(g) Me Me Et Me V^(h) Me Me Et Me —CH₂OC(═O)CH₂— Me Me Et Me—CH₂C(═O)CH₂— Me Me Et Me —CH₂C(═O)— Me Me Et Me —CH₂— Et Et Et Me—CH₂CH₂— Et Et Et Me —CH₂CH₂CH₂— Et Et Et Me —CH₂CH₂CH₂CH₂— Et Et Et Me—CH₂OCH₂CH₂— Et Et Et Me —CH₂CH₂OCH₂— Et Et Et Me —CH₂C(═O)CH₂CH₂— Et EtEt Me —CH₂CH₂C(═O)CH₂— Et Et Et Me —CH₂C(═S)CH₂CH₂— Et Et Et Me—CH₂CH₂C(═S)CH₂— Et Et Et Me —CH₂C(═O)CH₂— Et Et Et Me —CH₂C(═S)CH₂— EtEt Et Me —CH(Me)— Et Et Et Me —CH(OMe)— Et Et Et Me —CH(Me)CH₂— Et Et EtMe —CH₂CH(Me)— Et Et Et Me —CH₂CH(OMe)— Et Et Et Me —CH(Me)CH₂CH₂— Et EtEt Me —CH₂CH(Me)CH₂— Et Et Et Me —CH₂CH₂CH(Me)— Et Et Et Me —CH(Et)— EtEt Et Me —CH(Et)CH₂— Et Et Et Me —CH₂CH(Et)— Et Et Et Me —CH(Et)CH₂CH₂—Et Et Et Me —CH₂CH(Et)CH₂— Et Et Et Me —CH₂CH₂CH(Et)— Et Et Et Me—CH(OCF₃)— Et Et Et Me —CH(CF₃)— Et Et Et Me —CH₂CF₂CH₂— Et Et Et Me—CH₂CHFCH₂— Et Et Et Me —CH₂CF₂— Et Et Et Me —CH₂CHF— Et Et Et Me—CH(CN)— Et Et Et Me V^(a) Et Et Et Me V^(b) Et Et Et Me V^(c) Et Et EtMe V^(d) Et Et Et Me V^(e) Et Et Et Me V^(f) Et Et Et Me V^(g) Et Et EtMe V^(h) Et Et Et Me —CH₂OC(═O)CH₂— Et Et Et Me —CH₂C(═O)CH₂— Et Et EtMe —CH₂C(═O)— Et Et Et Me —CH₂— Me Et i-Pr Me —CH₂CH₂— Me Et i-Pr Me—CH₂CH₂CH₂— Me Et i-Pr Me —CH₂CH₂CH₂CH₂— Me Et i-Pr Me —CH₂OCH₂CH₂— MeEt i-Pr Me —CH₂CH₂OCH₂— Me Et i-Pr Me —CH₂C(═O)CH₂CH₂— Me Et i-Pr Me—CH₂CH₂C(═O)CH₂— Me Et i-Pr Me —CH₂C(═S)CH₂CH₂— Me Et i-Pr Me—CH₂CH₂C(═S)CH₂— Me Et i-Pr Me —CH₂C(═O)CH₂— Me Et i-Pr Me —CH₂C(═S)CH₂—Me Et i-Pr Me —CH(Me)— Me Et i-Pr Me —CH(OMe)— Me Et i-Pr Me —CH(Me)CH₂—Me Et i-Pr Me —CH₂CH(Me)— Me Et i-Pr Me —CH₂CH(OMe)— Me Et i-Pr Me—CH(Me)CH₂CH₂— Me Et i-Pr Me —CH₂CH(Me)CH₂— Me Et i-Pr Me —CH₂CH₂CH(Me)—Me Et i-Pr Me —CH(Et)— Me Et i-Pr Me —CH(Et)CH₂— Me Et i-Pr Me—CH₂CH(Et)— Me Et i-Pr Me —CH(Et)CH₂CH₂— Me Et i-Pr Me —CH₂CH(Et)CH₂— MeEt i-Pr Me —CH₂CH₂CH(Et)— Me Et i-Pr Me —CH(OCF₃)— Me Et i-Pr Me—CH(CF₃)— Me Et i-Pr Me —CH₂CF₂CH₂— Me Et i-Pr Me —CH₂CHFCH₂— Me Et i-PrMe —CH₂CF₂— Me Et i-Pr Me —CH₂CHF— Me Et i-Pr Me —CH(CN)— Me Et i-Pr MeV^(a) Me Et i-Pr Me V^(b) Me Et i-Pr Me V^(c) Me Et i-Pr Me V^(d) Me Eti-Pr Me V^(e) Me Et i-Pr Me V^(f) Me Et i-Pr Me V^(g) Me Et i-Pr MeV^(h) Me Et i-Pr Me —CH₂OC(═O)CH₂— Me Et i-Pr Me —CH₂C(═O)CH₂— Me Eti-Pr Me —CH₂C(═O)— Me Et i-Pr Me —CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂— Me Me4-Cl—Ph Me —CH₂CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂CH₂CH₂— Me Me 4-Cl—Ph Me—CH₂OCH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂OCH₂— Me Me 4-Cl—Ph Me—CH₂C(═O)CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂C(═O)CH₂— Me Me 4-Cl—Ph Me—CH₂C(═S)CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂C(═S)CH₂— Me Me 4-Cl—Ph Me—CH₂C(═O)CH₂— Me Me 4-Cl—Ph Me —CH₂C(═S)CH₂— Me Me 4-Cl—Ph Me —CH(Me)—Me Me 4-Cl—Ph Me —CH(OMe)— Me Me 4-Cl—Ph Me —CH(Me)CH₂— Me Me 4-Cl—Ph Me—CH₂CH(Me)— Me Me 4-Cl—Ph Me —CH₂CH(OMe)— Me Me 4-Cl—Ph Me—CH(Me)CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH(Me)CH₂— Me Me 4-Cl—Ph Me—CH₂CH₂CH(Me)— Me Me 4-Cl—Ph Me —CH(Et)— Me Me 4-Cl—Ph Me —CH(Et)CH₂— MeMe 4-Cl—Ph Me —CH₂CH(Et)— Me Me 4-Cl—Ph Me —CH(Et)CH₂CH₂— Me Me 4-Cl—PhMe —CH₂CH(Et)CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂CH(Et)— Me Me 4-Cl—Ph Me—CH(OCF₃)— Me Me 4-Cl—Ph Me —CH(CF₃)— Me Me 4-Cl—Ph Me —CH₂CF₂CH₂— Me Me4-Cl—Ph Me —CH₂CHFCH₂— Me Me 4-Cl—Ph Me —CH₂CF₂— Me Me 4-Cl—Ph Me—CH₂CHF— Me Me 4-Cl—Ph Me —CH(CN)— Me Me 4-Cl—Ph Me V^(a) Me Me 4-Cl—PhMe V^(b) Me Me 4-Cl—Ph Me V^(c) Me Me 4-Cl—Ph Me V^(d) Me Me 4-Cl—Ph MeV^(e) Me Me 4-Cl—Ph Me V^(f) Me Me 4-Cl—Ph Me V^(g) Me Me 4-Cl—Ph MeV^(h) Me Me 4-Cl—Ph Me —CH₂OC(═O)CH₂— Me Me 4-Cl—Ph Me —CH₂C(═O)CH₂— MeMe 4-Cl—Ph Me —CH₂C(═O)— Me Me 4-Cl—Ph Me —CH₂— Me Me 2-Cl—Ph Me—CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂CH₂CH₂— MeMe 2-Cl—Ph Me —CH₂OCH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂OCH₂— Me Me 2-Cl—PhMe —CH₂C(═O)CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂C(═O)CH₂— Me Me 2-Cl—Ph Me—CH₂C(═S)CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂C(═S)CH₂— Me Me 2-Cl—Ph Me—CH₂C(═O)CH₂— Me Me 2-Cl—Ph Me —CH₂C(═S)CH₂— Me Me 2-Cl—Ph Me —CH(Me)—Me Me 2-Cl—Ph Me —CH(OMe)— Me Me 2-Cl—Ph Me —CH(Me)CH₂— Me Me 2-Cl—Ph Me—CH₂CH(Me)— Me Me 2-Cl—Ph Me —CH₂CH(OMe)— Me Me 2-Cl—Ph Me—CH(Me)CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH(Me)CH₂— Me Me 2-Cl—Ph Me—CH₂CH₂CH(Me)— Me Me 2-Cl—Ph Me —CH(Et)— Me Me 2-Cl—Ph Me —CH(Et)CH₂— MeMe 2-Cl—Ph Me —CH₂CH(Et)— Me Me 2-Cl—Ph Me —CH(Et)CH₂CH₂— Me Me 2-Cl—PhMe —CH₂CH(Et)CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂CH(Et)— Me Me 2-Cl—Ph Me—CH(OCF₃)— Me Me 2-Cl—Ph Me —CH(CF₃)— Me Me 2-Cl—Ph Me —CH₂CF₂CH₂— Me Me2-Cl—Ph Me —CH₂CHFCH₂— Me Me 2-Cl—Ph Me —CH₂CF₂— Me Me 2-Cl—Ph Me—CH₂CHF— Me Me 2-Cl—Ph Me —CH(CN)— Me Me 2-Cl—Ph Me V^(a) Me Me 2-Cl—PhMe V^(b) Me Me 2-Cl—Ph Me V^(c) Me Me 2-Cl—Ph Me V^(d) Me Me 2-Cl—Ph MeV^(e) Me Me 2-Cl—Ph Me V^(f) Me Me 2-Cl—Ph Me V^(g) Me Me 2-Cl—Ph MeV^(h) Me Me 2-Cl—Ph Me —CH₂OC(═O)CH₂— Me Me 2-Cl—Ph Me —CH₂C(═O)CH₂— MeMe 2-Cl—Ph Me —CH₂C(═O)— Me Me 2-Cl—Ph Me —CH₂CH(Et)— Me Me c-Pr Me—CH(Et)CH₂CH₂— Me Me c-Pr Me —CH₂CH(Et)CH₂— Me Me c-Pr Me —CH₂CH₂CH(Et)—Me Me c-Pr Me —CH(OCF₃)— Me Me c-Pr Me —CH(CF₃)— Me Me c-Pr Me—CH₂CF₂CH₂— Me Me c-Pr Me —CH₂CHFCH₂— Me Me c-Pr Me —CH₂CF₂— Me Me c-PrMe —CH₂CHF— Me Me c-Pr Me —CH(CN)— Me Me c-Pr Me V^(a) Me Me c-Pr MeV^(b) Me Me c-Pr Me V^(c) Me Me c-Pr Me V^(d) Me Me c-Pr Me V^(e) Me Mec-Pr Me V^(f) Me Me c-Pr Me V^(g) Me Me c-Pr Me V^(h) Me Me c-Pr Me—CH₂OC(═O)CH₂— Me Me c-Pr Me —CH₂C(═O)CH₂— Me Me c-Pr Me —CH₂C(═O)— MeMe c-Pr

TABLE 3

R¹ V¹ R^(10a) R^(10b) R^(10c) Cl —CH₂— Me Me Me Cl —CH₂CH₂— Me Me Me Cl—CH₂CH₂CH₂— Me Me Me Cl —CH₂CH₂CH₂CH₂— Me Me Me Cl —CH₂OCH₂CH₂— Me Me MeCl —CH₂CH₂OCH₂— Me Me Me Cl —CH₂C(═O)CH₂CH₂— Me Me Me Cl—CH₂CH₂C(═O)CH₂— Me Me Me Cl —CH₂C(═S)CH₂CH₂— Me Me Me Cl—CH₂CH₂C(═S)CH₂— Me Me Me Cl —CH₂C(═O)CH₂— Me Me Me Cl —CH₂C(═S)CH₂— MeMe Me Cl —CH(Me)— Me Me Me Cl —CH(OMe)— Me Me Me Cl —CH(Me)CH₂— Me Me MeCl —CH₂CH(Me)— Me Me Me Cl —CH₂CH(OMe)— Me Me Me Cl —CH(Me)CH₂CH₂— Me MeMe Cl —CH₂CH(Me)CH₂— Me Me Me Cl —CH₂CH₂CH(Me)— Me Me Me Cl —CH(Et)— MeMe Me Cl —CH(Et)CH₂— Me Me Me Cl —CH₂CH(Et)— Me Me Me Cl —CH(Et)CH₂CH₂—Me Me Me Cl —CH₂CH(Et)CH₂— Me Me Me Cl —CH₂CH₂CH(Et)— Me Me Me Cl—CH(OCF₃)— Me Me Me Cl —CH(CF₃)— Me Me Me Cl —CH₂CF₂CH₂— Me Me Me Cl—CH₂CHFCH₂— Me Me Me Cl —CH₂CF₂— Me Me Me Cl —CH₂CHF— Me Me Me Cl—CH(CN)— Me Me Me Cl V^(a) Me Me Me Cl V^(b) Me Me Me Cl V^(c) Me Me MeCl V^(d) Me Me Me Cl V^(e) Me Me Me Cl V^(f) Me Me Me Cl V^(g) Me Me MeCl V^(h) Me Me Me Cl —CH₂OC(═O)CH₂— Me Me Me Cl —CH₂C(═O)CH₂— Me Me MeCl —CH₂C(═O)— Me Me Me Cl —CH₂— Me Me Et Cl —CH₂CH₂— Me Me Et Cl—CH₂CH₂CH₂— Me Me Et Cl —CH₂CH₂CH₂CH₂— Me Me Et Cl —CH₂OCH₂CH₂— Me Me EtCl —CH₂CH₂OCH₂— Me Me Et Cl —CH₂C(═O)CH₂CH₂— Me Me Et Cl—CH₂CH₂C(═O)CH₂— Me Me Et Cl —CH₂C(═S)CH₂CH₂— Me Me Et Cl—CH₂CH₂C(═S)CH₂— Me Me Et Cl —CH₂C(═O)CH₂— Me Me Et Cl —CH₂C(═S)CH₂— MeMe Et Cl —CH(Me)— Me Me Et Cl —CH(OMe)— Me Me Et Cl —CH(Me)CH₂— Me Me EtCl —CH₂CH(Me)— Me Me Et Cl —CH₂CH(OMe)— Me Me Et Cl —CH(Me)CH₂CH₂— Me MeEt Cl —CH₂CH(Me)CH₂— Me Me Et Cl —CH₂CH₂CH(Me)— Me Me Et Cl —CH(Et)— MeMe Et Cl —CH(Et)CH₂— Me Me Et Cl —CH₂CH(Et)— Me Me Et Cl —CH(Et)CH₂CH₂—Me Me Et Cl —CH₂CH(Et)CH₂— Me Me Et Cl —CH₂CH₂CH(Et)— Me Me Et Cl—CH(OCF₃)— Me Me Et Cl —CH(CF₃)— Me Me Et Cl —CH₂CF₂CH₂— Me Me Et Cl—CH₂CHFCH₂— Me Me Et Cl —CH₂CF₂— Me Me Et Cl —CH₂CHF— Me Me Et Cl—CH(CN)— Me Me Et Cl V^(a) Me Me Et Cl V^(b) Me Me Et Cl V^(c) Me Me EtCl V^(d) Me Me Et Cl V^(e) Me Me Et Cl V^(f) Me Me Et Cl V^(g) Me Me EtCl V^(h) Me Me Et Cl —CH₂OC(═O)CH₂— Me Me Et Cl —CH₂C(═O)CH₂— Me Me EtCl —CH₂C(═O)— Me Me Et Cl —CH₂— Me Et Et Cl —CH₂CH₂— Me Et Et Cl—CH₂CH₂CH₂— Me Et Et Cl —CH₂CH₂CH₂CH₂— Me Et Et Cl —CH₂OCH₂CH₂— Me Et EtCl —CH₂CH₂OCH₂— Me Et Et Cl —CH₂C(═O)CH₂CH₂— Me Et Et Cl—CH₂CH₂C(═O)CH₂— Me Et Et Cl —CH₂C(═S)CH₂CH₂— Me Et Et Cl—CH₂CH₂C(═S)CH₂— Me Et Et Cl —CH₂C(═O)CH₂— Me Et Et Cl —CH₂C(═S)CH₂— MeEt Et Cl —CH(Me)— Me Et Et Cl —CH(OMe)— Me Et Et Cl —CH(Me)CH₂— Me Et EtCl —CH₂CH(Me)— Me Et Et Cl —CH₂CH(OMe)— Me Et Et Cl —CH(Me)CH₂CH₂— Me EtEt Cl —CH₂CH(Me)CH₂— Me Et Et Cl —CH₂CH₂CH(Me)— Me Et Et Cl —CH(Et)— MeEt Et Cl —CH(Et)CH₂— Me Et Et Cl —CH₂CH(Et)— Me Et Et Cl —CH(Et)CH₂CH₂—Me Et Et Cl —CH₂CH(Et)CH₂— Me Et Et Cl —CH₂CH₂CH(Et)— Me Et Et Cl—CH(OCF₃)— Me Et Et Cl —CH(CF₃)— Me Et Et Cl —CH₂CF₂CH₂— Me Et Et Cl—CH₂CHFCH₂— Me Et Et Cl —CH₂CF₂— Me Et Et Cl —CH₂CHF— Me Et Et Cl—CH(CN)— Me Et Et Cl V^(a) Me Et Et Cl V^(b) Me Et Et Cl V^(c) Me Et EtCl V^(d) Me Et Et Cl V^(e) Me Et Et Cl V^(f) Me Et Et Cl V^(g) Me Et EtCl V^(h) Me Et Et Cl —CH₂OC(═O)CH₂— Me Et Et Cl —CH₂C(═O)CH₂— Me Et EtCl —CH₂C(═O)— Me Et Et Cl —CH₂— Et Et Et Cl —CH₂CH₂— Et Et Et Cl—CH₂CH₂CH₂— Et Et Et Cl —CH₂CH₂CH₂CH₂— Et Et Et Cl —CH₂OCH₂CH₂— Et Et EtCl —CH₂CH₂OCH₂— Et Et Et Cl —CH₂C(═O)CH₂CH₂— Et Et Et Cl—CH₂CH₂C(═O)CH₂— Et Et Et Cl —CH₂C(═S)CH₂CH₂— Et Et Et Cl—CH₂CH₂C(═S)CH₂— Et Et Et Cl —CH₂C(═O)CH₂— Et Et Et Cl —CH₂C(═S)CH₂— EtEt Et Cl —CH(Me)— Et Et Et Cl —CH(OMe)— Et Et Et Cl —CH(Me)CH₂— Et Et EtCl —CH₂CH(Me)— Et Et Et Cl —CH₂CH(OMe)— Et Et Et Cl —CH(Me)CH₂CH₂— Et EtEt Cl —CH₂CH(Me)CH₂— Et Et Et Cl —CH₂CH₂CH(Me)— Et Et Et Cl —CH(Et)— EtEt Et Cl —CH(Et)CH₂— Et Et Et Cl —CH₂CH(Et)— Et Et Et Cl —CH(Et)CH₂CH₂—Et Et Et Cl —CH₂CH(Et)CH₂— Et Et Et Cl —CH₂CH₂CH(Et)— Et Et Et Cl—CH(OCF₃)— Et Et Et Cl —CH(CF₃)— Et Et Et Cl —CH₂CF₂CH₂— Et Et Et Cl—CH₂CHFCH₂— Et Et Et Cl —CH₂CF₂— Et Et Et Cl —CH₂CHF— Et Et Et Cl—CH(CN)— Et Et Et Cl V^(a) Et Et Et Cl V^(b) Et Et Et Cl V^(c) Et Et EtCl V^(d) Et Et Et Cl V^(e) Et Et Et Cl V^(f) Et Et Et Cl V^(g) Et Et EtCl V^(h) Et Et Et Cl —CH₂OC(═O)CH₂— Et Et Et Cl —CH₂C(═O)CH₂— Et Et EtCl —CH₂C(═O)— Et Et Et Cl —CH₂— Me Me i-Pr Cl —CH₂CH₂— Me Me i-Pr Cl—CH₂CH₂CH₂— Me Me i-Pr Cl —CH₂CH₂CH₂CH₂— Me Me i-Pr Cl —CH₂OCH₂CH₂— MeMe i-Pr Cl —CH₂CH₂OCH₂— Me Me i-Pr Cl —CH₂C(═O)CH₂CH₂— Me Me i-Pr Cl—CH₂CH₂C(═O)CH₂— Me Me i-Pr Cl —CH₂C(═S)CH₂CH₂— Me Me i-Pr Cl—CH₂CH₂C(═S)CH₂— Me Me i-Pr Cl —CH₂C(═O)CH₂— Me Me i-Pr Cl —CH₂C(═S)CH₂—Me Me i-Pr Cl —CH(Me)— Me Me i-Pr Cl —CH(OMe)— Me Me i-Pr Cl —CH(Me)CH₂—Me Me i-Pr Cl —CH₂CH(Me)— Me Me i-Pr Cl —CH₂CH(OMe)— Me Me i-Pr Cl—CH(Me)CH₂CH₂— Me Me i-Pr Cl —CH₂CH(Me)CH₂— Me Me i-Pr Cl —CH₂CH₂CH(Me)—Me Me i-Pr Cl —CH(Et)— Me Me i-Pr Cl —CH(Et)CH₂— Me Me i-Pr Cl—CH₂CH(Et)— Me Me i-Pr Cl —CH(Et)CH₂CH₂— Me Me i-Pr Cl —CH₂CH(Et)CH₂— MeMe i-Pr Cl —CH₂CH₂CH(Et)— Me Me i-Pr Cl —CH(OCF₃)— Me Me i-Pr Cl—CH(CF₃)— Me Me i-Pr Cl —CH₂CF₂CH₂— Me Me i-Pr Cl —CH₂CHFCH₂— Me Me i-PrCl —CH₂CF₂— Me Me i-Pr Cl —CH₂CHF— Me Me i-Pr Cl —CH(CN)— Me Me i-Pr ClV^(a) Me Me i-Pr Cl V^(b) Me Me i-Pr Cl V^(c) Me Me i-Pr Cl V^(d) Me Mei-Pr Cl V^(e) Me Me i-Pr Cl V^(f) Me Me i-Pr Cl V^(g) Me Me i-Pr ClV^(h) Me Me i-Pr Cl —CH₂OC(═O)CH₂— Me Me i-Pr Cl —CH₂C(═O)CH₂— Me Mei-Pr Cl —CH₂C(═O)— Me Me i-Pr Cl —CH₂— Me Et i-Pr Cl —CH₂CH₂— Me Et i-PrCl —CH₂CH₂CH₂— Me Et i-Pr Cl —CH₂CH₂CH₂CH₂— Me Et i-Pr Cl —CH₂OCH₂CH₂—Me Et i-Pr Cl —CH₂CH₂OCH₂— Me Et i-Pr Cl —CH₂C(═O)CH₂CH₂— Me Et i-Pr Cl—CH₂CH₂C(═O)CH₂— Me Et i-Pr Cl —CH₂C(═S)CH₂CH₂— Me Et i-Pr Cl—CH₂CH₂C(═S)CH₂— Me Et i-Pr Cl —CH₂C(═O)CH₂— Me Et i-Pr Cl —CH₂C(═S)CH₂—Me Et i-Pr Cl —CH(Me)— Me Et i-Pr Cl —CH(OMe)— Me Et i-Pr Cl —CH(Me)CH₂—Me Et i-Pr Cl —CH₂CH(Me)— Me Et i-Pr Cl —CH₂CH(OMe)— Me Et i-Pr Cl—CH(Me)CH₂CH₂— Me Et i-Pr Cl —CH₂CH(Me)CH₂— Me Et i-Pr Cl —CH₂CH₂CH(Me)—Me Et i-Pr Cl —CH(Et)— Me Et i-Pr Cl —CH(Et)CH₂— Me Et i-Pr Cl—CH₂CH(Et)— Me Et i-Pr Cl —CH(Et)CH₂CH₂— Me Et i-Pr Cl —CH₂CH(Et)CH₂— MeEt i-Pr Cl —CH₂CH₂CH(Et)— Me Et i-Pr Cl —CH(OCF₃)— Me Et i-Pr Cl—CH(CF₃)— Me Et i-Pr Cl —CH₂CF₂CH₂— Me Et i-Pr Cl —CH₂CHFCH₂— Me Et i-PrCl —CH₂CF₂— Me Et i-Pr Cl —CH₂CHF— Me Et i-Pr Cl —CH(CN)— Me Et i-Pr ClV^(a) Me Et i-Pr Cl V^(b) Me Et i-Pr Cl V^(c) Me Et i-Pr Cl V^(d) Me Eti-Pr Cl V^(e) Me Et i-Pr Cl V^(f) Me Et i-Pr Cl V^(g) Me Et i-Pr ClV^(h) Me Et i-Pr Cl —CH₂OC(═O)CH₂— Me Et i-Pr Cl —CH₂C(═O)CH₂— Me Eti-Pr Cl —CH₂C(═O)— Me Et i-Pr Cl —CH₂— Me Me Ph Cl —CH₂CH₂— Me Me Ph Cl—CH₂CH₂CH₂— Me Me Ph Cl —CH₂CH₂CH₂CH₂— Me Me Ph Cl —CH₂OCH₂CH₂— Me Me PhCl —CH₂CH₂OCH₂— Me Me Ph Cl —CH₂C(═O)CH₂CH₂— Me Me Ph Cl—CH₂CH₂C(═O)CH₂— Me Me Ph Cl —CH₂C(═S)CH₂CH₂— Me Me Ph Cl—CH₂CH₂C(═S)CH₂— Me Me Ph Cl —CH₂C(═O)CH₂— Me Me Ph Cl —CH₂C(═S)CH₂— MeMe Ph Cl —CH(Me)— Me Me Ph Cl —CH(OMe)— Me Me Ph Cl —CH(Me)CH₂— Me Me PhCl —CH₂CH(Me)— Me Me Ph Cl —CH₂CH(OMe)— Me Me Ph Cl —CH(Me)CH₂CH₂— Me MePh Cl —CH₂CH(Me)CH₂— Me Me Ph Cl —CH₂CH₂CH(Me)— Me Me Ph Cl —CH(Et)— MeMe Ph Cl —CH(Et)CH₂— Me Me Ph Cl —CH₂CH(Et)— Me Me Ph Cl —CH(Et)CH₂CH₂—Me Me Ph Cl —CH₂CH(Et)CH₂— Me Me Ph Cl —CH₂CH₂CH(Et)— Me Me Ph Cl—CH(OCF₃)— Me Me Ph Cl —CH(CF₃)— Me Me Ph Cl —CH₂CF₂CH₂— Me Me Ph Cl—CH₂CHFCH₂— Me Me Ph Cl —CH₂CF₂— Me Me Ph Cl —CH₂CHF— Me Me Ph Cl—CH(CN)— Me Me Ph Cl V^(a) Me Me Ph Cl V^(b) Me Me Ph Cl V^(c) Me Me PhCl V^(d) Me Me Ph Cl V^(e) Me Me Ph Cl V^(f) Me Me Ph Cl V^(g) Me Me PhCl V^(h) Me Me Ph Cl —CH₂OC(═O)CH₂— Me Me Ph Cl —CH₂C(═O)CH₂— Me Me PhCl —CH₂C(═O)— Me Me Ph Cl —CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂— Me Me 4-Cl—PhCl —CH₂CH₂CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂CH₂CH₂— Me Me 4-Cl—Ph Cl—CH₂OCH₂CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂OCH₂— Me Me 4-Cl—Ph Cl—CH₂C(═O)CH₂CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂C(═O)CH₂— Me Me 4-Cl—Ph Cl—CH₂C(═S)CH₂CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂C(═S)CH₂— Me Me 4-Cl—Ph Cl—CH₂C(═O)CH₂— Me Me 4-Cl—Ph Cl —CH₂C(═S)CH₂— Me Me 4-Cl—Ph Cl —CH(Me)—Me Me 4-Cl—Ph Cl —CH(OMe)— Me Me 4-Cl—Ph Cl —CH(Me)CH₂— Me Me 4-Cl—Ph Cl—CH₂CH(Me)— Me Me 4-Cl—Ph Cl —CH₂CH(OMe)— Me Me 4-Cl—Ph Cl—CH(Me)CH₂CH₂— Me Me 4-Cl—Ph Cl —CH₂CH(Me)CH₂— Me Me 4-Cl—Ph Cl—CH₂CH₂CH(Me)— Me Me 4-Cl—Ph Cl —CH(Et)— Me Me 4-Cl—Ph Cl —CH(Et)CH₂— MeMe 4-Cl—Ph Cl —CH₂CH(Et)— Me Me 4-Cl—Ph Cl —CH(Et)CH₂CH₂— Me Me 4-Cl—PhCl —CH₂CH(Et)CH₂— Me Me 4-Cl—Ph Cl —CH₂CH₂CH(Et)— Me Me 4-Cl—Ph Cl—CH(OCF₃)— Me Me 4-Cl—Ph Cl —CH(CF₃)— Me Me 4-Cl—Ph Cl —CH₂CF₂CH₂— Me Me4-Cl—Ph Cl —CH₂CHFCH₂— Me Me 4-Cl—Ph Cl —CH₂CF₂— Me Me 4-Cl—Ph Cl—CH₂CHF— Me Me 4-Cl—Ph Cl —CH(CN)— Me Me 4-Cl—Ph Cl V^(a) Me Me 4-Cl—PhCl V^(b) Me Me 4-Cl—Ph Cl V^(c) Me Me 4-Cl—Ph Cl V^(d) Me Me 4-Cl—Ph ClV^(e) Me Me 4-Cl—Ph Cl V^(f) Me Me 4-Cl—Ph Cl V^(g) Me Me 4-Cl—Ph ClV^(h) Me Me 4-Cl—Ph Cl —CH₂OC(═O)CH₂— Me Me 4-Cl—Ph Cl —CH₂C(═O)CH₂— MeMe 4-Cl—Ph Cl —CH₂C(═O)— Me Me 4-Cl—Ph Cl —CH₂— Me Me 3-Cl—Ph Cl—CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂CH₂CH₂— MeMe 3-Cl—Ph Cl —CH₂OCH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂OCH₂— Me Me 3-Cl—PhCl —CH₂C(═O)CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂C(═O)CH₂— Me Me 3-Cl—Ph Cl—CH₂C(═S)CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂C(═S)CH₂— Me Me 3-Cl—Ph Cl—CH₂C(═O)CH₂— Me Me 3-Cl—Ph Cl —CH₂C(═S)CH₂— Me Me 3-Cl—Ph Cl —CH(Me)—Me Me 3-Cl—Ph Cl —CH(OMe)— Me Me 3-Cl—Ph Cl —CH(Me)CH₂— Me Me 3-Cl—Ph Cl—CH₂CH(Me)— Me Me 3-Cl—Ph Cl —CH₂CH(OMe)— Me Me 3-Cl—Ph Cl—CH(Me)CH₂CH₂— Me Me 3-Cl—Ph Cl —CH₂CH(Me)CH₂— Me Me 3-Cl—Ph Cl—CH₂CH₂CH(Me)— Me Me 3-Cl—Ph Cl —CH(Et)— Me Me 3-Cl—Ph Cl —CH(Et)CH₂— MeMe 3-Cl—Ph Cl —CH₂CH(Et)— Me Me 3-Cl—Ph Cl —CH(Et)CH₂CH₂— Me Me 3-Cl—PhCl —CH₂CH(Et)CH₂— Me Me 3-Cl—Ph Cl —CH₂CH₂CH(Et)— Me Me 3-Cl—Ph Cl—CH(OCF₃)— Me Me 3-Cl—Ph Cl —CH(CF₃)— Me Me 3-Cl—Ph Cl —CH₂CF₂CH₂— Me Me3-Cl—Ph Cl —CH₂CHFCH₂— Me Me 3-Cl—Ph Cl —CH₂CF₂— Me Me 3-Cl—Ph Cl—CH₂CHF— Me Me 3-Cl—Ph Cl —CH(CN)— Me Me 3-Cl—Ph Cl V^(a) Me Me 3-Cl—PhCl V^(b) Me Me 3-Cl—Ph Cl V^(c) Me Me 3-Cl—Ph Cl V^(d) Me Me 3-Cl—Ph ClV^(e) Me Me 3-Cl—Ph Cl V^(f) Me Me 3-Cl—Ph Cl V^(g) Me Me 3-Cl—Ph ClV^(h) Me Me 3-Cl—Ph Cl —CH₂OC(═O)CH₂— Me Me 3-Cl—Ph Cl —CH₂C(═O)CH₂— MeMe 3-Cl—Ph Cl —CH₂C(═O)— Me Me 3-Cl—Ph Cl —CH₂— Me Me 2-Cl—Ph Cl—CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂CH₂CH₂— MeMe 2-Cl—Ph Cl —CH₂OCH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂OCH₂— Me Me 2-Cl—PhCl —CH₂C(═O)CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂C(═O)CH₂— Me Me 2-Cl—Ph Cl—CH₂C(═S)CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂C(═S)CH₂— Me Me 2-Cl—Ph Cl—CH₂C(═O)CH₂— Me Me 2-Cl—Ph Cl —CH₂C(═S)CH₂— Me Me 2-Cl—Ph Cl —CH(Me)—Me Me 2-Cl—Ph Cl —CH(OMe)— Me Me 2-Cl—Ph Cl —CH(Me)CH₂— Me Me 2-Cl—Ph Cl—CH₂CH(Me)— Me Me 2-Cl—Ph Cl —CH₂CH(OMe)— Me Me 2-Cl—Ph Cl—CH(Me)CH₂CH₂— Me Me 2-Cl—Ph Cl —CH₂CH(Me)CH₂— Me Me 2-Cl—Ph Cl—CH₂CH₂CH(Me)— Me Me 2-Cl—Ph Cl —CH(Et)— Me Me 2-Cl—Ph Cl —CH(Et)CH₂— MeMe 2-Cl—Ph Cl —CH₂CH(Et)— Me Me 2-Cl—Ph Cl —CH(Et)CH₂CH₂— Me Me 2-Cl—PhCl —CH₂CH(Et)CH₂— Me Me 2-Cl—Ph Cl —CH₂CH₂CH(Et)— Me Me 2-Cl—Ph Cl—CH(OCF₃)— Me Me 2-Cl—Ph Cl —CH(CF₃)— Me Me 2-Cl—Ph Cl —CH₂CF₂CH₂— Me Me2-Cl—Ph Cl —CH₂CHFCH₂— Me Me 2-Cl—Ph Cl —CH₂CF₂— Me Me 2-Cl—Ph Cl—CH₂CHF— Me Me 2-Cl—Ph Cl —CH(CN)— Me Me 2-Cl—Ph Cl V^(a) Me Me 2-Cl—PhCl V^(b) Me Me 2-Cl—Ph Cl V^(c) Me Me 2-Cl—Ph Cl V^(d) Me Me 2-Cl—Ph ClV^(e) Me Me 2-Cl—Ph Cl V^(f) Me Me 2-Cl—Ph Cl V^(g) Me Me 2-Cl—Ph ClV^(h) Me Me 2-Cl—Ph Cl —CH₂OC(═O)CH₂— Me Me 2-Cl—Ph Cl —CH₂C(═O)CH₂— MeMe 2-Cl—Ph Cl —CH₂C(═O)— Me Me 2-Cl—Ph Cl —CH₂— Me Me c-Pr Cl —CH₂CH₂—Me Me c-Pr Cl —CH₂CH₂CH₂— Me Me c-Pr Cl —CH₂CH₂CH₂CH₂— Me Me c-Pr Cl—CH₂OCH₂CH₂— Me Me c-Pr Cl —CH₂CH₂OCH₂— Me Me c-Pr Cl —CH₂C(═O)CH₂CH₂—Me Me c-Pr Cl —CH₂CH₂C(═O)CH₂— Me Me c-Pr Cl —CH₂C(═S)CH₂CH₂— Me Me c-PrCl —CH₂CH₂C(═S)CH₂— Me Me c-Pr Cl —CH₂C(═O)CH₂— Me Me c-Pr Cl—CH₂C(═S)CH₂— Me Me c-Pr Cl —CH(Me)— Me Me c-Pr Cl —CH(OMe)— Me Me c-PrCl —CH(Me)CH₂— Me Me c-Pr Cl —CH₂CH(Me)— Me Me c-Pr Cl —CH₂CH(OMe)— MeMe c-Pr Cl —CH(Me)CH₂CH₂— Me Me c-Pr Cl —CH₂CH(Me)CH₂— Me Me c-Pr Cl—CH₂CH₂CH(Me)— Me Me c-Pr Cl —CH(Et)— Me Me c-Pr Cl —CH(Et)CH₂— Me Mec-Pr Cl —CH₂CH(Et)— Me Me c-Pr Cl —CH(Et)CH₂CH₂— Me Me c-Pr Cl—CH₂CH(Et)CH₂— Me Me c-Pr Cl —CH₂CH₂CH(Et)— Me Me c-Pr Cl —CH(OCF₃)— MeMe c-Pr Cl —CH(CF₃)— Me Me c-Pr Cl —CH₂CF₂CH₂— Me Me c-Pr Cl —CH₂CHFCH₂—Me Me c-Pr Cl —CH₂CF₂— Me Me c-Pr Cl —CH₂CHF— Me Me c-Pr Cl —CH(CN)— MeMe c-Pr Cl V^(a) Me Me c-Pr Cl V^(b) Me Me c-Pr Cl V^(c) Me Me c-Pr ClV^(d) Me Me c-Pr Cl V^(e) Me Me c-Pr Cl V^(f) 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—CH₂— Me Me i-Pr F —CH₂CH₂— Me Me i-Pr F —CH₂CH₂CH₂— Me Me i-Pr F—CH₂CH₂CH₂CH₂— Me Me i-Pr F —CH₂OCH₂CH₂— Me Me i-Pr F —CH₂CH₂OCH₂— Me Mei-Pr F —CH₂C(═O)CH₂CH₂— Me Me i-Pr F —CH₂CH₂C(═O)CH₂— Me Me i-Pr F—CH₂C(═S)CH₂CH₂— Me Me i-Pr F —CH₂CH₂C(═S)CH₂— Me Me i-Pr F—CH₂C(═O)CH₂— Me Me i-Pr F —CH₂C(═S)CH₂— Me Me i-Pr F —CH(Me)— Me Mei-Pr F —CH(OMe)— Me Me i-Pr F —CH(Me)CH₂— Me Me i-Pr F —CH₂CH(Me)— Me Mei-Pr F —CH₂CH(OMe)— Me Me i-Pr F —CH(Me)CH₂CH₂— Me Me i-Pr F—CH₂CH(Me)CH₂— Me Me i-Pr F —CH₂CH₂CH(Me)— Me Me i-Pr F —CH(Et)— Me Mei-Pr F —CH(Et)CH₂— Me Me i-Pr F —CH₂CH(Et)— Me Me i-Pr F —CH(Et)CH₂CH₂—Me Me i-Pr F —CH₂CH(Et)CH₂— Me Me i-Pr F —CH₂CH₂CH(Et)— Me Me i-Pr F—CH(OCF₃)— Me Me i-Pr F —CH(CF₃)— Me Me i-Pr F —CH₂CF₂CH₂— Me Me i-Pr F—CH₂CHFCH₂— Me Me i-Pr F —CH₂CF₂— Me Me i-Pr F —CH₂CHF— Me Me i-Pr F—CH(CN)— Me Me i-Pr F V^(a) Me Me i-Pr F V^(b) Me Me i-Pr F V^(c) Me Mei-Pr F V^(d) Me Me i-Pr F V^(e) Me Me i-Pr F V^(f) Me Me i-Pr F V^(g) MeMe i-Pr F V^(h) Me Me i-Pr F —CH₂OC(═O)CH₂— Me Me i-Pr F —CH₂C(═O)CH₂—Me Me i-Pr F —CH₂C(═O)— Me Me i-Pr F —CH₂— Me Et i-Pr F —CH₂CH₂— Me Eti-Pr F —CH₂CH₂CH₂— Me Et i-Pr F —CH₂CH₂CH₂CH₂— Me Et i-Pr F —CH₂OCH₂CH₂—Me Et i-Pr F —CH₂CH₂OCH₂— Me Et i-Pr F —CH₂C(═O)CH₂CH₂— Me Et i-Pr F—CH₂CH₂C(═O)CH₂— Me Et i-Pr F —CH₂C(═S)CH₂CH₂— Me Et i-Pr F—CH₂CH₂C(═S)CH₂— Me Et i-Pr F —CH₂C(═O)CH₂— Me Et i-Pr F —CH₂C(═S)CH₂—Me Et i-Pr F —CH(Me)— Me Et i-Pr F —CH(OMe)— Me Et i-Pr F —CH(Me)CH₂— MeEt i-Pr F —CH₂CH(Me)— Me Et i-Pr F —CH₂CH(OMe)— Me Et i-Pr F—CH(Me)CH₂CH₂— Me Et i-Pr F —CH₂CH(Me)CH₂— Me Et i-Pr F —CH₂CH₂CH(Me)—Me Et i-Pr F —CH(Et)— Me Et i-Pr F —CH(Et)CH₂— Me Et i-Pr F —CH₂CH(Et)—Me Et i-Pr F —CH(Et)CH₂CH₂— Me Et i-Pr F —CH₂CH(Et)CH₂— Me Et i-Pr F—CH₂CH₂CH(Et)— Me Et i-Pr F —CH(OCF₃)— Me Et i-Pr F —CH(CF₃)— Me Et i-PrF —CH₂CF₂CH₂— Me Et i-Pr F —CH₂CHFCH₂— Me Et i-Pr F —CH₂CF₂— Me Et i-PrF —CH₂CHF— Me Et i-Pr F —CH(CN)— Me Et i-Pr F V^(a) Me Et i-Pr F V^(b)Me Et i-Pr F V^(c) Me Et i-Pr F V^(d) Me Et i-Pr F V^(e) Me Et i-Pr FV^(f) Me Et i-Pr F V^(g) Me Et i-Pr F V^(h) Me Et i-Pr F —CH₂OC(═O)CH₂—Me Et i-Pr F —CH₂C(═O)CH₂— Me Et i-Pr F —CH₂C(═O)— Me Et i-Pr F —CH₂— MeMe Ph F —CH₂CH₂— Me Me Ph F —CH₂CH₂CH₂— Me Me Ph F —CH₂CH₂CH₂CH₂— Me MePh F —CH₂OCH₂CH₂— Me Me Ph F —CH₂CH₂OCH₂— Me Me Ph F —CH₂C(═O)CH₂CH₂— MeMe Ph F —CH₂CH₂C(═O)CH₂— Me Me Ph F —CH₂C(═S)CH₂CH₂— Me Me Ph F—CH₂CH₂C(═S)CH₂— Me Me Ph F —CH₂C(═O)CH₂— Me Me Ph F —CH₂C(═S)CH₂— Me MePh F —CH(Me)— Me Me Ph F —CH(OMe)— Me Me Ph F —CH(Me)CH₂— Me Me Ph F—CH₂CH(Me)— Me Me Ph F —CH₂CH(OMe)— Me Me Ph F —CH(Me)CH₂CH₂— Me Me Ph F—CH₂CH(Me)CH₂— Me Me Ph F —CH₂CH₂CH(Me)— Me Me Ph F —CH(Et)— Me Me Ph F—CH(Et)CH₂— Me Me Ph F —CH₂CH(Et)— Me Me Ph F —CH(Et)CH₂CH₂— Me Me Ph F—CH₂CH(Et)CH₂— Me Me Ph F —CH₂CH₂CH(Et)— Me Me Ph F —CH(OCF₃)— Me Me PhF —CH(CF₃)— Me Me Ph F —CH₂CF₂CH₂— Me Me Ph F —CH₂CHFCH₂— Me Me Ph F—CH₂CF₂— Me Me Ph F —CH₂CHF— Me Me Ph F —CH(CN)— Me Me Ph F V^(a) Me MePh F V^(b) Me Me Ph F V^(c) Me Me Ph F V^(d) Me Me Ph F V^(e) Me Me Ph FV^(f) Me Me Ph F V^(g) Me Me Ph F V^(h) Me Me Ph F —CH₂OC(═O)CH₂— Me MePh F —CH₂C(═O)CH₂— Me Me Ph F —CH₂C(═O)— Me Me Ph F —CH₂— Me Me 4-Cl—PhF —CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH₂CH₂— MeMe 4-Cl—Ph F —CH₂OCH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂OCH₂— Me Me 4-Cl—Ph F—CH₂C(═O)CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂C(═O)CH₂— Me Me 4-Cl—Ph F—CH₂C(═S)CH₂CH₂— Me Me 4-Cl—Ph F —CH₂CH₂C(═S)CH₂— Me Me 4-Cl—Ph F—CH₂C(═O)CH₂— Me Me 4-Cl—Ph F —CH₂C(═S)CH₂— Me Me 4-Cl—Ph F —CH(Me)— MeMe 4-Cl—Ph F —CH(OMe)— Me Me 4-Cl—Ph F —CH(Me)CH₂— Me Me 4-Cl—Ph F—CH₂CH(Me)— Me Me 4-Cl—Ph F —CH₂CH(OMe)— Me Me 4-Cl—Ph F —CH(Me)CH₂CH₂—Me Me 4-Cl—Ph F —CH₂CH(Me)CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH(Me)— Me Me4-Cl—Ph F —CH(Et)— Me Me 4-Cl—Ph F —CH(Et)CH₂— Me Me 4-Cl—Ph F—CH₂CH(Et)— Me Me 4-Cl—Ph F —CH(Et)CH₂CH₂— Me Me 4-Cl—Ph F—CH₂CH(Et)CH₂— Me Me 4-Cl—Ph F —CH₂CH₂CH(Et)— Me Me 4-Cl—Ph F —CH(OCF₃)—Me Me 4-Cl—Ph F —CH(CF₃)— Me Me 4-Cl—Ph F —CH₂CF₂CH₂— Me Me 4-Cl—Ph F—CH₂CHFCH₂— Me Me 4-Cl—Ph F —CH₂CF₂— Me Me 4-Cl—Ph F —CH₂CHF— Me Me4-Cl—Ph F —CH(CN)— Me Me 4-Cl—Ph F V^(a) Me Me 4-Cl—Ph F V^(b) Me Me4-Cl—Ph F V^(c) Me Me 4-Cl—Ph F V^(d) Me Me 4-Cl—Ph F V^(e) Me Me4-Cl—Ph F V^(f) Me Me 4-Cl—Ph F V^(g) Me Me 4-Cl—Ph F V^(h) Me Me4-Cl—Ph F —CH₂OC(═O)CH₂— Me Me 4-Cl—Ph F —CH₂C(═O)CH₂— Me Me 4-Cl—Ph F—CH₂C(═O)— Me Me 4-Cl—Ph F —CH₂— Me Me 3-Cl—Ph F —CH₂CH₂— Me Me 3-Cl—PhF —CH₂CH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂CH₂CH₂— Me Me 3-Cl—Ph F—CH₂OCH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂OCH₂— Me Me 3-Cl—Ph F—CH₂C(═O)CH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂C(═O)CH₂— Me Me 3-Cl—Ph F—CH₂C(═S)CH₂CH₂— Me Me 3-Cl—Ph F —CH₂CH₂C(═S)CH₂— Me Me 3-Cl—Ph F—CH₂C(═O)CH₂— Me Me 3-Cl—Ph F —CH₂C(═S)CH₂— Me Me 3-Cl—Ph F —CH(Me)— MeMe 3-Cl—Ph F —CH(OMe)— Me Me 3-Cl—Ph F —CH(Me)CH₂— Me Me 3-Cl—Ph F—CH₂CH(Me)— Me Me 3-Cl—Ph F —CH₂CH(OMe)— Me Me 3-Cl—Ph F —CH(Me)CH₂CH₂—Me Me 3-Cl—Ph F —CH₂CH(Me)CH₂— Me Me 3-Cl—Ph F —CH₂CH₂CH(Me)— Me Me3-Cl—Ph F —CH(Et)— Me Me 3-Cl—Ph F —CH(Et)CH₂— Me Me 3-Cl—Ph F—CH₂CH(Et)— Me Me 3-Cl—Ph F —CH(Et)CH₂CH₂— Me Me 3-Cl—Ph F—CH₂CH(Et)CH₂— Me Me 3-Cl—Ph F —CH₂CH₂CH(Et)— Me Me 3-Cl—Ph F —CH(OCF₃)—Me Me 3-Cl—Ph F —CH(CF₃)— Me Me 3-Cl—Ph F —CH₂CF₂CH₂— Me Me 3-Cl—Ph F—CH₂CHFCH₂— Me Me 3-Cl—Ph F —CH₂CF₂— Me Me 3-Cl—Ph F —CH₂CHF— Me Me3-Cl—Ph F —CH(CN)— Me Me 3-Cl—Ph F V^(a) Me Me 3-Cl—Ph F V^(b) Me Me3-Cl—Ph F V^(c) Me Me 3-Cl—Ph F V^(d) Me Me 3-Cl—Ph F V^(e) Me Me3-Cl—Ph F V^(f) Me Me 3-Cl—Ph F V^(g) Me Me 3-Cl—Ph F V^(h) Me Me3-Cl—Ph F —CH₂OC(═O)CH₂— Me Me 3-Cl—Ph F —CH₂C(═O)CH₂— Me Me 3-Cl—Ph F—CH₂C(═O)— Me Me 3-Cl—Ph F —CH₂— Me Me 2-Cl—Ph F —CH₂CH₂— Me Me 2-Cl—PhF —CH₂CH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂CH₂CH₂— Me Me 2-Cl—Ph F—CH₂OCH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂OCH₂— Me Me 2-Cl—Ph F—CH₂C(═O)CH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂C(═O)CH₂— Me Me 2-Cl—Ph F—CH₂C(═S)CH₂CH₂— Me Me 2-Cl—Ph F —CH₂CH₂C(═S)CH₂— Me Me 2-Cl—Ph F—CH₂C(═O)CH₂— Me Me 2-Cl—Ph F —CH₂C(═S)CH₂— Me Me 2-Cl—Ph F —CH(Me)— MeMe 2-Cl—Ph F —CH(OMe)— Me Me 2-Cl—Ph F —CH(Me)CH₂— Me Me 2-Cl—Ph F—CH₂CH(Me)— Me Me 2-Cl—Ph F —CH₂CH(OMe)— Me Me 2-Cl—Ph F —CH(Me)CH₂CH₂—Me Me 2-Cl—Ph F —CH₂CH(Me)CH₂— Me Me 2-Cl—Ph F —CH₂CH₂CH(Me)— Me Me2-Cl—Ph F —CH(Et)— Me Me 2-Cl—Ph F —CH(Et)CH₂— Me Me 2-Cl—Ph F—CH₂CH(Et)— Me Me 2-Cl—Ph F —CH(Et)CH₂CH₂— Me Me 2-Cl—Ph F—CH₂CH(Et)CH₂— Me Me 2-Cl—Ph F —CH₂CH₂CH(Et)— Me Me 2-Cl—Ph F —CH(OCF₃)—Me Me 2-Cl—Ph F —CH(CF₃)— Me Me 2-Cl—Ph F —CH₂CF₂CH₂— Me Me 2-Cl—Ph F—CH₂CHFCH₂— Me Me 2-Cl—Ph F —CH₂CF₂— Me Me 2-Cl—Ph F —CH₂CHF— Me Me2-Cl—Ph F —CH(CN)— Me Me 2-Cl—Ph F V^(a) Me Me 2-Cl—Ph F V^(b) Me Me2-Cl—Ph F V^(c) Me Me 2-Cl—Ph F V^(d) Me Me 2-Cl—Ph F V^(e) Me Me2-Cl—Ph F V^(f) Me Me 2-Cl—Ph F V^(g) Me Me 2-Cl—Ph F V^(h) Me Me2-Cl—Ph F —CH₂OC(═O)CH₂— Me Me 2-Cl—Ph F —CH₂C(═O)CH₂— Me Me 2-Cl—Ph F—CH₂C(═O)— Me Me 2-Cl—Ph F —CH₂— Me Me c-Pr F —CH₂CH₂— Me Me c-Pr F—CH₂CH₂CH₂— Me Me c-Pr F —CH₂CH₂CH₂CH₂— Me Me c-Pr F —CH₂OCH₂CH₂— Me Mec-Pr F —CH₂CH₂OCH₂— Me Me c-Pr F —CH₂C(═O)CH₂CH₂— Me Me c-Pr F—CH₂CH₂C(═O)CH₂— Me Me c-Pr F —CH₂C(═S)CH₂CH₂— Me Me c-Pr F—CH₂CH₂C(═S)CH₂— Me Me c-Pr F —CH₂C(═O)CH₂— Me Me c-Pr F —CH₂C(═S)CH₂—Me Me c-Pr F —CH(Me)— Me Me c-Pr F —CH(OMe)— Me Me c-Pr F —CH(Me)CH₂— MeMe c-Pr F —CH₂CH(Me)— Me Me c-Pr F —CH₂CH(OMe)— Me Me c-Pr F—CH(Me)CH₂CH₂— Me Me c-Pr F —CH₂CH(Me)CH₂— Me Me c-Pr F —CH₂CH₂CH(Me)—Me Me c-Pr F —CH(Et)— Me Me c-Pr F —CH(Et)CH₂— Me Me c-Pr F —CH₂CH(Et)—Me Me c-Pr F —CH(Et)CH₂CH₂— Me Me c-Pr F —CH₂CH(Et)CH₂— Me Me c-Pr F—CH₂CH₂CH(Et)— Me Me c-Pr F —CH(OCF₃)— Me Me c-Pr F —CH(CF₃)— Me Me c-PrF —CH₂CF₂CH₂— Me Me c-Pr F —CH₂CHFCH₂— Me Me c-Pr F —CH₂CF₂— Me Me c-PrF —CH₂CHF— Me Me c-Pr F —CH(CN)— Me Me c-Pr F V^(a) Me Me c-Pr F V^(b)Me Me c-Pr F V^(c) Me Me c-Pr F V^(d) Me Me c-Pr F V^(e) Me Me c-Pr FV^(f) Me Me c-Pr F V^(g) Me Me c-Pr F V^(h) Me Me c-Pr F —CH₂OC(═O)CH₂—Me Me c-Pr F —CH₂C(═O)CH₂— Me Me c-Pr F —CH₂C(═O)— Me Me c-Pr Me —CH₂—Me Me Et Me —CH₂CH₂— Me Me Et Me —CH₂CH₂CH₂— Me Me Et Me —CH₂CH₂CH₂CH₂—Me Me Et Me —CH₂OCH₂CH₂— Me Me Et Me —CH₂CH₂OCH₂— Me Me Et Me—CH₂C(═O)CH₂CH₂— Me Me Et Me —CH₂CH₂C(═O)CH₂— Me Me Et Me—CH₂C(═S)CH₂CH₂— Me Me Et Me —CH₂CH₂C(═S)CH₂— Me Me Et Me 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i-Pr Me —CH₂C(═S)CH₂CH₂— Me Et i-Pr Me—CH₂CH₂C(═S)CH₂— Me Et i-Pr Me —CH₂C(═O)CH₂— Me Et i-Pr Me —CH₂C(═S)CH₂—Me Et i-Pr Me —CH(Me)— Me Et i-Pr Me —CH(OMe)— Me Et i-Pr Me —CH(Me)CH₂—Me Et i-Pr Me —CH₂CH(Me)— Me Et i-Pr Me —CH₂CH(OMe)— Me Et i-Pr Me—CH(Me)CH₂CH₂— Me Et i-Pr Me —CH₂CH(Me)CH₂— Me Et i-Pr Me —CH₂CH₂CH(Me)—Me Et i-Pr Me —CH(Et)— Me Et i-Pr Me —CH(Et)CH₂— Me Et i-Pr Me—CH₂CH(Et)— Me Et i-Pr Me —CH(Et)CH₂CH₂— Me Et i-Pr Me —CH₂CH(Et)CH₂— MeEt i-Pr Me —CH₂CH₂CH(Et)— Me Et i-Pr Me —CH(OCF₃)— Me Et i-Pr Me—CH(CF₃)— Me Et i-Pr Me —CH₂CF₂CH₂— Me Et i-Pr Me —CH₂CHFCH₂— Me Et i-PrMe —CH₂CF₂— Me Et i-Pr Me —CH₂CHF— Me Et i-Pr Me —CH(CN)— Me Et i-Pr MeV^(a) Me Et i-Pr Me V^(b) Me Et i-Pr Me V^(c) Me Et i-Pr Me V^(d) Me Eti-Pr Me V^(e) Me Et i-Pr Me V^(f) Me Et i-Pr Me V^(g) Me Et i-Pr MeV^(h) Me Et i-Pr Me —CH₂OC(═O)CH₂— Me Et i-Pr Me —CH₂C(═O)CH₂— Me Eti-Pr Me —CH₂C(═O)— Me Et i-Pr Me —CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂— Me Me4-Cl—Ph Me —CH₂CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂CH₂CH₂— Me Me 4-Cl—Ph Me—CH₂OCH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂OCH₂— Me Me 4-Cl—Ph Me—CH₂C(═O)CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂C(═O)CH₂— Me Me 4-Cl—Ph Me—CH₂C(═S)CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂C(═S)CH₂— Me Me 4-Cl—Ph Me—CH₂C(═O)CH₂— Me Me 4-Cl—Ph Me —CH₂C(═S)CH₂— Me Me 4-Cl—Ph Me —CH(Me)—Me Me 4-Cl—Ph Me —CH(OMe)— Me Me 4-Cl—Ph Me —CH(Me)CH₂— Me Me 4-Cl—Ph Me—CH₂CH(Me)— Me Me 4-Cl—Ph Me —CH₂CH(OMe)— Me Me 4-Cl—Ph Me—CH(Me)CH₂CH₂— Me Me 4-Cl—Ph Me —CH₂CH(Me)CH₂— Me Me 4-Cl—Ph Me—CH₂CH₂CH(Me)— Me Me 4-Cl—Ph Me —CH(Et)— Me Me 4-Cl—Ph Me —CH(Et)CH₂— MeMe 4-Cl—Ph Me —CH₂CH(Et)— Me Me 4-Cl—Ph Me —CH(Et)CH₂CH₂— Me Me 4-Cl—PhMe —CH₂CH(Et)CH₂— Me Me 4-Cl—Ph Me —CH₂CH₂CH(Et)— Me Me 4-Cl—Ph Me—CH(OCF₃)— Me Me 4-Cl—Ph Me —CH(CF₃)— Me Me 4-Cl—Ph Me —CH₂CF₂CH₂— Me Me4-Cl—Ph Me —CH₂CHFCH₂— Me Me 4-Cl—Ph Me —CH₂CF₂— Me Me 4-Cl—Ph Me—CH₂CHF— Me Me 4-Cl—Ph Me —CH(CN)— Me Me 4-Cl—Ph Me V^(a) Me Me 4-Cl—PhMe V^(b) Me Me 4-Cl—Ph Me V^(c) Me Me 4-Cl—Ph Me V^(d) Me Me 4-Cl—Ph MeV^(e) Me Me 4-Cl—Ph Me V^(f) Me Me 4-Cl—Ph Me V^(g) Me Me 4-Cl—Ph MeV^(h) Me Me 4-Cl—Ph Me —CH₂OC(═O)CH₂— Me Me 4-Cl—Ph Me —CH₂C(═O)CH₂— MeMe 4-Cl—Ph Me —CH₂C(═O)— Me Me 4-Cl—Ph Me —CH₂— Me Me 2-Cl—Ph Me—CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂CH₂CH₂— MeMe 2-Cl—Ph Me —CH₂OCH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂OCH₂— Me Me 2-Cl—PhMe —CH₂C(═O)CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂C(═O)CH₂— Me Me 2-Cl—Ph Me—CH₂C(═S)CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂C(═S)CH₂— Me Me 2-Cl—Ph Me—CH₂C(═O)CH₂— Me Me 2-Cl—Ph Me —CH₂C(═S)CH₂— Me Me 2-Cl—Ph Me —CH(Me)—Me Me 2-Cl—Ph Me —CH(OMe)— Me Me 2-Cl—Ph Me —CH(Me)CH₂— Me Me 2-Cl—Ph Me—CH₂CH(Me)— Me Me 2-Cl—Ph Me —CH₂CH(OMe)— Me Me 2-Cl—Ph Me—CH(Me)CH₂CH₂— Me Me 2-Cl—Ph Me —CH₂CH(Me)CH₂— Me Me 2-Cl—Ph Me—CH₂CH₂CH(Me)— Me Me 2-Cl—Ph Me —CH(Et)— Me Me 2-Cl—Ph Me —CH(Et)CH₂— MeMe 2-Cl—Ph Me —CH₂CH(Et)— Me Me 2-Cl—Ph Me —CH(Et)CH₂CH₂— Me Me 2-Cl—PhMe —CH₂CH(Et)CH₂— Me Me 2-Cl—Ph Me —CH₂CH₂CH(Et)— Me Me 2-Cl—Ph Me—CH(OCF₃)— Me Me 2-Cl—Ph Me —CH(CF₃)— Me Me 2-Cl—Ph Me —CH₂CF₂CH₂— Me Me2-Cl—Ph Me —CH₂CHFCH₂— Me Me 2-Cl—Ph Me —CH₂CF₂— Me Me 2-Cl—Ph Me—CH₂CHF— Me Me 2-Cl—Ph Me —CH(CN)— Me Me 2-Cl—Ph Me V^(a) Me Me 2-Cl—PhMe V^(b) Me Me 2-Cl—Ph Me V^(c) Me Me 2-Cl—Ph Me V^(d) Me Me 2-Cl—Ph MeV^(e) Me Me 2-Cl—Ph Me V^(f) Me Me 2-Cl—Ph Me V^(g) Me Me 2-Cl—Ph MeV^(h) Me Me 2-Cl—Ph Me —CH₂OC(═O)CH₂— Me Me 2-Cl—Ph Me —CH₂C(═O)CH₂— MeMe 2-Cl—Ph Me —CH₂C(═O)— Me Me 2-Cl—Ph Me —CH₂CH(Et)— Me Me c-Pr Me—CH(Et)CH₂CH₂— Me Me c-Pr Me —CH₂CH(Et)CH₂— Me Me c-Pr Me —CH₂CH₂CH(Et)—Me Me c-Pr Me —CH(OCF₃)— Me Me c-Pr Me —CH(CF₃)— Me Me c-Pr Me—CH₂CF₂CH₂— Me Me c-Pr Me —CH₂CHFCH₂— Me Me c-Pr Me —CH₂CF₂— Me Me c-PrMe —CH₂CHF— Me Me c-Pr Me —CH(CN)— Me Me c-Pr Me V^(a) Me Me c-Pr MeV^(b) Me Me c-Pr Me V^(e) Me Me c-Pr Me V^(d) Me Me c-Pr Me V^(e) Me Mec-Pr Me V^(f) Me Me c-Pr Me V^(g) Me Me c-Pr Me V^(h) Me Me c-Pr Me—CH₂OC(═O)CH₂— Me Me c-Pr Me —CH₂C(═O)CH₂— Me Me c-Pr Me —CH₂C(═O)— MeMe c-Pr

TABLE 4

R² R³ 2-OCF₃ H 3-OCF₃ H 4-OCF₃ H 2-OCF₂H H 3-OCF₂H H 4-OCF₂H H 2-OCFH₂ H3-OCFH₂ H 4-OCFH₂ H 2-OCF₃ 3-F 2-OCF₃ 4-F 2-OCF₃ 5-F 2-OCF₃ 6-F 3-OCF₃2-F 3-OCF₃ 4-F 3-OCF₃ 5-F 3-OCF₃ 6-F 4-OCF₃ 2-F 4-OCF₃ 3-F 4-OCF₃ 5-F4-OCF₃ 6-F 2-OCF₂H 3-F 2-OCF₂H 4-F 2-OCF₂H 5-F 2-OCF₂H 6-F 3-OCF₂H 2-F3-OCF₂H 4-F 3-OCF₂H 5-F 3-OCF₂H 6-F 4-OCFH₂ 2-F 4-OCFH₂ 3-F 4-OCFH₂ 5-F4-OCFH₂ 6-F 3-OCFH₂ 2-F 3-OCFH₂ 4-F 3-OCFH₂ 5-F 3-OCFH₂ 6-F 2-OCF₃ 3-Cl2-OCF₃ 4-Cl 2-OCF₃ 5-Cl 2-OCF₃ 6-Cl 3-OCF₃ 2-Cl 3-OCF₃ 4-Cl 3-OCF₃ 5-Cl3-OCF₃ 6-Cl 4-OCF₃ 2-Cl 4-OCF₃ 3-Cl 4-OCF₃ 5-Cl 4-OCF₃ 6-Cl 2-OCF₂H 3-Cl2-OCF₂H 4-Cl 2-OCF₂H 5-Cl 2-OCF₂H 6-Cl 3-OCF₂H 2-Cl 3-OCF₂H 4-Cl 3-OCF₂H5-Cl 3-OCF₂H 6-Cl 4-OCFH₂ 2-Cl 4-OCFH₂ 3-Cl 4-OCFH₂ 5-Cl 4-OCFH₂ 6-Cl3-OCFH₂ 2-Cl 3-OCFH₂ 4-Cl 3-OCFH₂ 5-Cl 3-OCFH₂ 6-Cl 2-OCF₃ 3-Me 2-OCF₃4-Me 2-OCF₃ 5-Me 2-OCF₃ 6-Me 3-OCF₃ 2-Me 3-OCF₃ 4-Me 3-OCF₃ 5-Me 3-OCF₃6-Me 4-OCF₃ 2-Me 4-OCF₃ 3-Me 4-OCF₃ 5-Me 4-OCF₃ 6-Me 2-OCF₂H 3-Me2-OCF₂H 4-Me 2-OCF₂H 5-Me 2-OCF₂H 6-Me 3-OCF₂H 2-Me 3-OCF₂H 4-Me 3-OCF₂H5-Me 3-OCF₂H 6-Me 4-OCFH₂ 2-Me 4-OCFH₂ 3-Me 4-OCFH₂ 5-Me 4-OCFH₂ 6-Me3-OCFH₂ 2-Me 3-OCFH₂ 4-Me 3-OCFH₂ 5-Me 3-OCFH₂ 6-Me 2-OCF₃ 3-CN 2-OCF₃4-CN 2-OCF₃ 5-CN 2-OCF₃ 6-CN 3-OCF₃ 2-CN 3-OCF₃ 4-CN 3-OCF₃ 5-CN 3-OCF₃6-CN 4-OCF₃ 2-CN 4-OCF₃ 3-CN 4-OCF₃ 5-CN 4-OCF₃ 6-CN 2-OCF₂H 3-CN2-OCF₂H 4-CN 2-OCF₂H 5-CN 2-OCF₂H 6-CN 3-OCF₂H 2-CN 3-OCF₂H 4-CN 3-OCF₂H5-CN 3-OCF₂H 6-CN 4-OCFH₂ 2-CN 4-OCFH₂ 3-CN 4-OCFH₂ 5-CN 4-OCFH₂ 6-CN3-OCFH₂ 2-CN 3-OCFH₂ 4-CN 3-OCFH₂ 5-CN 3-OCFH₂ 6-CN 2-SiMe₃ H 3-SiMe₃ H4-SiMe₃ H 2-CH₂SiMe₃ H 3-CH₂SiMe₃ H 4-CH₂SiMe₃ H 2-SiMe₃ 3-F 2-SiMe₃ 4-F2-SiMe₃ 5-F 2-SiMe₃ 6-F 3-SiMe₃ 2-F 3-SiMe₃ 4-F 3-SiMe₃ 5-F 3-SiMe₃ 6-F4-SiMe₃ 2-F 4-SiMe₃ 3-F 4-SiMe₃ 5-F 2-CH₂SiMe₃ 3-F 2-CH₂SiMe₃ 4-F2-CH₂SiMe₃ 5-F 2-CH₂SiMe₃ 6-F 3-CH₂SiMe₃ 2-F 3-CH₂SiMe₃ 4-F 3-CH₂SiMe₃5-F 3-CH₂SiMe₃ 6-F 4-CH₂SiMe₃ 2-F 4-CH₂SiMe₃ 3-F 4-CH₂SiMe₃ 5-F4-CH₂SiMe₃ 6-F 2-SiMe₃ 3-Cl 2-SiMe₃ 4-Cl 2-SiMe₃ 5-Cl 2-SiMe₃ 6-Cl3-SiMe₃ 2-Cl 3-SiMe₃ 4-Cl 3-SiMe₃ 5-Cl 3-SiMe₃ 6-Cl 4-SiMe₃ 2-Cl 4-SiMe₃3-Cl 4-SiMe₃ 5-Cl 4-SiMe₃ 6-Cl 2-CH₂SiMe₃ 3-Cl 2-CH₂SiMe₃ 4-Cl2-CH₂SiMe₃ 5-Cl 2-CH₂SiMe₃ 6-Cl 3-CH₂SiMe₃ 2-Cl 3-CH₂SiMe₃ 4-Cl3-CH₂SiMe₃ 5-Cl 3-CH₂SiMe₃ 6-Cl 4-CH₂SiMe₃ 2-Cl 4-CH₂SiMe₃ 3-Cl4-CH₂SiMe₃ 5-Cl 4-CH₂SiMe₃ 6-Cl 2-SiMe₃ 3-Me 2-SiMe₃ 4-Me 2-SiMe₃ 5-Me2-SiMe₃ 6-Me 3-SiMe₃ 2-Me 3-SiMe₃ 4-Me 3-SiMe₃ 5-Me 3-SiMe₃ 6-Me 4-SiMe₃2-Me 4-SiMe₃ 3-Me 4-SiMe₃ 5-Me 4-SiMe₃ 6-Me 2-CH₂SiMe₃ 3-Me 2-CH₂SiMe₃4-Me 2-CH₂SiMe₃ 5-Me 2-CH₂SiMe₃ 6-Me 3-CH₂SiMe₃ 2-Me 3-CH₂SiMe₃ 4-Me3-CH₂SiMe₃ 5-Me 3-CH₂SiMe₃ 6-Me 4-CH₂SiMe₃ 2-Me 4-CH₂SiMe₃ 3-Me4-CH₂SiMe₃ 5-Me 4-CH₂SiMe₃ 6-Me 2-SiMe₃ 3-CN 2-SiMe₃ 4-CN 2-SiMe₃ 5-CN2-SiMe₃ 6-CN 3-SiMe₃ 2-CN 3-SiMe₃ 4-CN 3-SiMe₃ 5-CN 3-SiMe₃ 6-CN 4-SiMe₃2-CN 4-SiMe₃ 5-CN 4-SiMe₃ 6-CN 2-CH₂SiMe₃ 3-CN 2-CH₂SiMe₃ 4-CN2-CH₂SiMe₃ 5-CN 2-CH₂SiMe₃ 6-CN 3-CH₂SiMe₃ 2-CN 3-CH₂SiMe₃ 4-CN3-CH₂SiMe₃ 5-CN 3-CH₂SiMe₃ 6-CN 4-CH₂SiMe₃ 2-CN 4-CH₂SiMe₃ 3-CN4-CH₂SiMe₃ 5-CN 4-CH₂SiMe₃ 6-CN 2-SiMe₂Et H 3-SiMe₂Et H 4-SiMe₂Et H2-SiMe₂Et 3-F 2-SiMe₂Et 4-F 2-SiMe₂Et 5-F 2-SiMe₂Et 6-F 3-SiMe₂Et 2-F3-SiMe₂Et 4-F 3-SiMe₂Et 5-F 3-SiMe₂Et 6-F 4-SiMe₂Et 2-F 4-SiMe₂Et 3-F4-SiMe₂Et 5-F 4-SiMe₂Et 6-F 2-SiMe₂Et 3-Cl 2-SiMe₂Et 4-Cl 2-SiMe₂Et 5-Cl2-SiMe₂Et 6-Cl 3-SiMe₂Et 2-Cl 3-SiMe₂Et 4-Cl 3-SiMe₂Et 5-Cl 3-SiMe₂Et6-Cl 4-SiMe₂Et 2-Cl 4-SiMe₂Et 3-Cl 4-SiMe₂Et 5-Cl 4-SiMe₂Et 6-Cl2-SiMe₂Et 3-Me 2-SiMe₂Et 4-Me 2-SiMe₂Et 5-Me 2-SiMe₂Et 6-Me 3-SiMe₂Et2-Me 3-SiMe₂Et 4-Me 3-SiMe₂Et 5-Me 3-SiMe₂Et 6-Me 4-SiMe₂Et 2-Me4-SiMe₂Et 3-Me 4-SiMe₂Et 5-Me 4-SiMe₂Et 6-Me 2-SiMe₂Et 3-CN 2-SiMe₂Et4-CN 2-SiMe₂Et 5-CN 2-SiMe₂Et 6-CN 3-SiMe₂Et 2-CN 3-SiMe₂Et 4-CN3-SiMe₂Et 5-CN 3-SiMe₂Et 6-CN 4-SiMe₂Et 2-CN 4-SiMe₂Et 3-CN 4-SiMe₂Et5-CN 4-SiMe₂Et 6-CN 4-SiMe₃ 6-F 4-SiMe₃ 3-CN

TABLE 5

R¹ R⁴ Q R^(14a) R^(14b) Cl MeO —CH₂— 4-Cl—Ph H Cl MeO —CH₂— 3-Cl—Ph H ClMeO —CH₂— 2-Cl—Ph H Cl MeO —CH₂— 4-Br—Ph H Cl MeO —CH₂— 3-Br—Ph H Cl MeO—CH₂— 2-Br—Ph H Cl MeO —CH₂— 4-Et—Ph H Cl MeO —CH₂— 3-Et—Ph H Cl MeO—CH₂— 2-Et—Ph H Cl MeO —CH₂— 4-CN—Ph H Cl MeO —CH₂— 3-CN—Ph H Cl MeO—CH₂— 2-CN—Ph H Cl MeO —CH₂— 4-CF₃—Ph H Cl MeO —CH₂— 3-CF₃—Ph H Cl MeO—CH₂— 2-CF₃—Ph H Cl MeO —CH₂— 4-Ac—Ph H Cl MeO —CH₂— 3-Ac—Ph H Cl MeO—CH₂— 2-Ac—Ph H Cl MeO —CH₂— 4-MeO—Ph H Cl MeO —CH₂— 3-MeO—Ph H Cl MeO—CH₂— 2-MeO—Ph H Cl MeO —CH₂— 4-i-PrO—Ph H Cl MeO —CH₂— 3-i-PrO—Ph H ClMeO —CH₂— 2-i-PrO—Ph H Cl MeO —CH₂— 4-I—Ph H Cl MeO —CH₂— 3-I—Ph H ClMeO —CH₂— 2-I—Ph H Cl MeO —CH₂— 4-Me(C═NH)—Ph H Cl MeO —CH₂—3-Me(C═NH)—Ph H Cl MeO —CH₂— 2-Me(C═NH)—Ph H Cl MeO —CH₂—4-Me(C═NOMe)—Ph H Cl MeO —CH₂— 3-Me(C═NOMe)—Ph H Cl MeO —CH₂—2-Me(C═NOMe)—Ph H Cl MeO —CH₂— 4-MeNH(C═O)—Ph H Cl MeO —CH₂—3-MeNH(C═O)—Ph H Cl MeO —CH₂— 2-MeNH(C═O)—Ph H Cl MeO —CH₂— 2,6-di-Cl—PhH Cl MeO —CH₂— 2,5-di-Cl—Ph H Cl MeO —CH₂— 2,4-di-Cl—Ph H Cl MeO —CH₂—3,3-di-Cl—Ph H Cl MeO —CH₂— 3,4-di-Cl—Ph H Cl MeO —CH₂— 2,6-di-Me—Ph HCl MeO —CH₂— 2,5-di-Me—Ph H Cl MeO —CH₂— 2,4-di-Me—Ph H Cl MeO —CH₂—3,3-di-Me—Ph H Cl MeO —CH₂— 3,4-di-Me—Ph H Cl MeO —CH₂— 2,6-di-CF₃O—Ph HCl MeO —CH₂— 2,5-di-CF₃O—Ph H Cl MeO —CH₂— 2,4-di-CF₃O—Ph H Cl MeO —CH₂—3,3-di-CF₃O—Ph H Cl MeO —CH₂— 3,4-di-CF₃O—Ph H Cl MeO —CH₂— 4-CF₂—Ph HCl MeO —CH₂— 3-CF₂—Ph H Cl MeO —CH₂— 2-CF₂—Ph H Cl MeO —CH₂— 2-F-3-Cl—PhH Cl MeO —CH₂— 2-F-4-Cl—Ph H Cl MeO —CH₂— 2-F-5-Cl—Ph H Cl MeO —CH₂—2-F-6-Cl—Ph H Cl MeO —CH₂— 3-F-2-Cl—Ph H Cl MeO —CH₂— 3-F-4-Cl—Ph H ClMeO —CH₂— 3-F-5-Cl—Ph H Cl MeO —CH₂— 3-F-6-Cl—Ph H Cl MeO —CH₂—4-F-3-Cl—Ph H Cl MeO —CH₂— 4-F-2-Cl—Ph H Cl MeO —CH₂— pyrid-2-yl H ClMeO —CH₂— pyrid-4-yl H Cl MeO —CH₂— 3-CF₃-pyrid-2-yl H Cl MeO —CH₂—4-CF₃-pyrid-2-yl H Cl MeO —CH₂— 5-CF₃-pyrid-2-yl H Cl MeO —CH₂—6-CF₃-pyrid-2-yl H Cl MeO —CH₂— 2-CF₃-pyrid-4-yl H Cl MeO —CH₂—3-CF₃-pyrid-4-yl H Cl MeO —CH₂— 3-Me-pyrid-2-yl H Cl MeO —CH₂—4-Me-pyrid-2-yl H Cl MeO —CH₂— 5-Me-pyrid-2-yl H Cl MeO —CH₂—6-Me-pyrid-2-yl H Cl MeO —CH₂— 5-Cl-thien-2-yl H Cl MeO —CH₂—4-Cl-thien-2-yl H Cl MeO —CH₂— 3-Cl-thien-2-yl H Cl MeO —CH₂—5-CF₃-thien-2-yl H Cl MeO —CH₂— 4-CF₃-thien-2-yl H Cl MeO —CH₂—3-CF₃-thien-2-yl H Cl MeO —CH₂— 5-Cl-thien-3-yl H Cl MeO —CH₂—4-Cl-thien-3-yl H Cl MeO —CH₂— 2-Cl-thien-3-yl H Cl MeO —CH₂—5-CF₃-thien-3-yl H Cl MeO —CH₂— 4-CF₃-thien-3-yl H Cl MeO —CH₂—2-CF₃-thien-3-yl H Cl MeO —CH₂— thien-2-yl H Cl MeO —CH₂— 4-Cl-benzyl HCl MeO —CH₂— 3-Cl-benzyl H Cl MeO —CH₂— 2-Cl-benzyl H Cl MeO —CH₂—4-Br-benzyl H Cl MeO —CH₂— 3-Br-benzyl H Cl MeO —CH₂— 2-Br-benzyl H ClMeO —CH₂— 4-Et-benzyl H Cl MeO —CH₂— 3-Et-benzyl H Cl MeO —CH₂—2-Et-benzyl H Cl MeO —CH₂— 4-CN-benzyl H Cl MeO —CH₂— 3-CN-benzyl H ClMeO —CH₂— 2-CN-benzyl H Cl MeO —CH₂— 4-CF₃-benzyl H Cl MeO —CH₂—3-CF₃-benzyl H Cl MeO —CH₂— 2-CF₃-benzyl H Cl MeO —CH₂— 4-CHF₂-benzyl HCl MeO —CH₂— 3-CHF₂-benzyl H Cl MeO —CH₂— 2-CHF₂-benzyl H Cl MeO —CH₂—4-Ac-benzyl H Cl MeO —CH₂— 3-Ac-benzyl H Cl MeO —CH₂— 2-Ac-benzyl H ClMeO —CH₂— 4-MeO-benzyl H Cl MeO —CH₂— 3-MeO-benzyl H Cl MeO —CH₂—2-MeO-benzyl H Cl MeO —CH₂— 4-i-PrO-benzyl H Cl MeO —CH₂— 3-i-PrO-benzylH Cl MeO —CH₂— 2-i-PrO-benzyl H Cl MeO —CH₂— benzyl H Cl MeO —CH₂—methyl H Cl MeO —CH₂— n-propyl H Cl MeO —CH₂— i-propyl H Cl MeO —CH₂—c-propyl H Cl MeO —CH₂— n-pentyl H Cl MeO —CH₂— c-pentyl H Cl MeO —CH₂—n-heptyl H Cl MeO —CH₂— 1-naphthyl H Cl MeO N 4-Cl—Ph H Cl MeO N 3-Cl—PhH Cl MeO N 2-Cl—Ph H Cl MeO N 4-Br—Ph H Cl MeO N 3-Br—Ph H Cl MeO N2-Br—Ph H Cl MeO N 4-Et—Ph H Cl MeO N 3-Et—Ph H Cl MeO N 2-Et—Ph H ClMeO N 4-CN—Ph H Cl MeO N 3-CN—Ph H Cl MeO N 2-CN—Ph H Cl MeO N 4-CF₃—PhH Cl MeO N 3-CF₃—Ph H Cl MeO N 2-CF₃—Ph H Cl MeO N 4-Ac—Ph H Cl MeO N3-Ac—Ph H Cl MeO N 2-Ac—Ph H Cl MeO N 4-MeO—Ph H Cl MeO N 3-MeO—Ph H ClMeO N 2-MeO—Ph H Cl MeO N 4-i-PrO—Ph H Cl MeO N 3-i-PrO—Ph H Cl MeO N2-i-PrO—Ph H Cl MeO N 4-Cl-benzyl H Cl MeO N 3-Cl-benzyl H Cl MeO N2-Cl-benzyl H Cl MeO N 4-Br-benzyl H Cl MeO N 3-Br-benzyl H Cl MeO N2-Br-benzyl H Cl MeO N 4-Et-benzyl H Cl MeO N 3-Et-benzyl H Cl MeO N2-Et-benzyl H Cl MeO N 4-CN-benzyl H Cl MeO N 3-CN-benzyl H Cl MeO N2-CN-benzyl H Cl MeO N 4-CF₃-benzyl H Cl MeO N 3-CF₃-benzyl H Cl MeO N2-CF₃-benzyl H Cl MeO N 4-CHF₂-benzyl H Cl MeO N 3-CHF₂-benzyl H Cl MeON 2-CHF₂-benzyl H Cl MeO N 4-Ac-benzyl H Cl MeO N 3-Ac-benzyl H Cl MeO N2-Ac-benzyl H Cl MeO N 4-MeO-benzyl H Cl MeO N 3-MeO-benzyl H Cl MeO N2-MeO-benzyl H Cl MeO N 4-i-PrO-benzyl H Cl MeO N 3-i-PrO-benzyl H ClMeO N 2-i-PrO-benzyl H Cl MeO O 4-Cl—Ph H Cl MeO O 3-Cl—Ph H Cl MeO O2-Cl—Ph H Cl MeO O 4-Br—Ph H Cl MeO O 3-Br—Ph H Cl MeO O 2-Br—Ph H ClMeO O 4-Et—Ph H Cl MeO O 3-Et—Ph H Cl MeO O 2-Et—Ph H Cl MeO O 4-CN—Ph HCl MeO O 3-CN—Ph H Cl MeO O 2-CN—Ph H Cl MeO O 4-CF₃—Ph H Cl MeO O3-CF₃—Ph H Cl MeO O 2-CF₃—Ph H Cl MeO O 4-Ac—Ph H Cl MeO O 3-Ac—Ph H ClMeO O 2-Ac—Ph H Cl MeO O 4-MeO—Ph H Cl MeO O 3-MeO—Ph H Cl MeO O2-MeO—Ph H Cl MeO O 4-Cl-benzyl H Cl MeO O 3-Cl-benzyl H Cl MeO O2-Cl-benzyl H Cl MeO O 4-Br-benzyl H Cl MeO O 3-Br-benzyl H Cl MeO O2-Br-benzyl H Cl MeO O 4-Et-benzyl H Cl MeO O 3-Et-benzyl H Cl MeO O2-Et-benzyl H Cl MeO O 4-CN-benzyl H Cl MeO O 3-CN-benzyl H Cl MeO O2-CN-benzyl H Cl MeO O 4-CF₃-benzyl H Cl MeO O 3-CF₃-benzyl H Cl MeO O2-CF₃-benzyl H Cl MeO O 4-CHF₂-benzyl H Cl MeO O 3-CHF₂-benzyl H Cl MeOO 2-CHF₂-benzyl H Cl MeO O 4-Ac-benzyl H Cl MeO O 3-Ac-benzyl H Cl MeO O2-Ac-benzyl H Cl MeO O 4-MeO-benzyl H Cl MeO O 3-MeO-benzyl H Cl MeO O2-MeO-benzyl H Cl MeO O 4-i-PrO-benzyl H Cl MeO O 3-i-PrO-benzyl H ClMeO O 2-i-PrO-benzyl H Me MeO —CH₂— 4-Cl—Ph H Me MeO —CH₂— 3-Cl—Ph H MeMeO —CH₂— 2-Cl—Ph H Me MeO —CH₂— 4-Br—Ph H Me MeO —CH₂— 3-Br—Ph H Me MeO—CH₂— 2-Br—Ph H Me MeO —CH₂— 4-Et—Ph H Me MeO —CH₂— 3-Et—Ph H Me MeO—CH₂— 2-Et—Ph H Me MeO —CH₂— 4-CN—Ph H Me MeO —CH₂— 3-CN—Ph H Me MeO—CH₂— 2-CN—Ph H Me MeO —CH₂— 4-CF₃—Ph H Me MeO —CH₂— 3-CF₃—Ph H Me MeO—CH₂— 2-CF₃—Ph H Me MeO —CH₂— 4-Ac—Ph H Me MeO —CH₂— 3-Ac—Ph H Me MeO—CH₂— 2-Ac—Ph H Me MeO —CH₂— 4-MeO—Ph H Me MeO —CH₂— 3-MeO—Ph H Me MeO—CH₂— 2-MeO—Ph H Me MeO —CH₂— 4-i-PrO—Ph H Me MeO —CH₂— 3-i-PrO—Ph H MeMeO —CH₂— 2-i-PrO—Ph H Me MeO —CH₂— 4-Cl-benzyl H Me MeO —CH₂—3-Cl-benzyl H Me MeO —CH₂— 2-Cl-benzyl H Me MeO —CH₂— 4-Br-benzyl H MeMeO —CH₂— 3-Br-benzyl H Me MeO —CH₂— 2-Br-benzyl H Me MeO —CH₂—4-Et-benzyl H Me MeO —CH₂— 3-Et-benzyl H Me MeO —CH₂— 2-Et-benzyl H MeMeO —CH₂— 4-CN-benzyl H Me MeO —CH₂— 3-CN-benzyl H Me MeO —CH₂—2-CN-benzyl H Me MeO —CH₂— 4-CF₃-benzyl H Me MeO —CH₂— 3-CF₃-benzyl H MeMeO —CH₂— 2-CF₃-benzyl H Me MeO —CH₂— 4-CHF₂-benzyl H Me MeO —CH₂—3-CHF₂-benzyl H Me MeO —CH₂— 2-CHF₂-benzyl H Me MeO —CH₂— 4-Ac-benzyl HMe MeO —CH₂— 3-Ac-benzyl H Me MeO —CH₂— 2-Ac-benzyl H Me MeO —CH₂—4-MeO-benzyl H Me MeO —CH₂— 3-MeO-benzyl H Me MeO —CH₂— 2-MeO-benzyl HMe MeO —CH₂— 4-i-PrO-benzyl H Me MeO —CH₂— 3-i-PrO-benzyl H Me MeO —CH₂—2-i-PrO-benzyl H Cl MeO —CH₂— 4-Cl—Ph Me Cl MeO —CH₂— 3-Cl—Ph Me Cl MeO—CH₂— 2-Cl—Ph Me Cl MeO —CH₂— 4-Br—Ph Me Cl MeO —CH₂— 3-Br—Ph Me Cl MeO—CH₂— 2-Br—Ph Me Cl MeO —CH₂— 4-Et—Ph Me Cl MeO —CH₂— 3-Et—Ph Me Cl MeO—CH₂— 2-Et—Ph Me Cl MeO —CH₂— 4-CN—Ph Me Cl MeO —CH₂— 3-CN—Ph Me Cl MeO—CH₂— 2-CN—Ph Me Cl MeO —CH₂— 4-CF₃—Ph Me Cl MeO —CH₂— 3-CF₃—Ph Me ClMeO —CH₂— 2-CF₃—Ph Me Cl MeO —CH₂— 4-Ac—Ph Me Cl MeO —CH₂— 3-Ac—Ph Me ClMeO —CH₂— 2-Ac—Ph Me Cl MeO —CH₂— 4-MeO—Ph Me Cl MeO —CH₂— 3-MeO—Ph MeCl MeO —CH₂— 2-MeO—Ph Me Cl MeO —CH₂— 4-i-PrO—Ph Me Cl MeO —CH₂—3-i-PrO—Ph Me Cl MeO —CH₂— 2-i-PrO—Ph Me Cl MeO —CH₂— 4-Cl-benzyl H ClMeO —CH₂— 3-Cl-benzyl H Cl MeO —CH₂— 2-Cl-benzyl H Cl MeO —CH₂—4-Br-benzyl H Cl MeO —CH₂— 3-Br-benzyl H Cl MeO —CH₂— 2-Br-benzyl H ClMeO —CH₂— 4-Et-benzyl H Cl MeO —CH₂— 3-Et-benzyl H Cl MeO —CH₂—2-Et-benzyl H Cl MeO —CH₂— 4-CN-benzyl H Cl MeO —CH₂— 3-CN-benzyl H ClMeO —CH₂— 2-CN-benzyl H Cl MeO —CH₂— 4-CF₃-benzyl H Cl MeO —CH₂—3-CF₃-benzyl H Cl MeO —CH₂— 2-CF₃-benzyl H Cl MeO —CH₂— 4-CHF₂-benzyl HCl MeO —CH₂— 3-CHF₂-benzyl H Cl MeO —CH₂— 2-CHF₂-benzyl H Cl MeO —CH₂—4-Ac-benzyl H Cl MeO —CH₂— 3-Ac-benzyl H Cl MeO —CH₂— 2-Ac-benzyl H ClMeO —CH₂— 4-MeO-benzyl H Cl MeO —CH₂— 3-MeO-benzyl H Cl MeO —CH₂—2-MeO-benzyl H Cl MeNH —CH₂— 4-i-PrO-benzyl H Cl MeNH —CH₂—3-i-PrO-benzyl H Cl MeNH —CH₂— 2-i-PrO-benzyl H Cl MeNH —CH₂— 4-Cl—Ph HCl MeNH —CH₂— 3-Cl—Ph H Cl MeNH —CH₂— 2-Cl—Ph H Cl MeNH —CH₂— 4-Br—Ph HCl MeNH —CH₂— 3-Br—Ph H Cl MeNH —CH₂— 2-Br—Ph H Cl MeNH —CH₂— 4-Et—Ph HCl MeNH —CH₂— 3-Et—Ph H Cl MeNH —CH₂— 2-Et—Ph H Cl MeNH —CH₂— 4-CN—Ph HCl MeNH —CH₂— 3-CN—Ph H Cl MeNH —CH₂— 2-CN—Ph H Cl MeNH —CH₂— 4-CF₃—Ph HCl MeNH —CH₂— 3-CF₃—Ph H Cl MeNH —CH₂— 2-CF₃—Ph H Cl MeNH —CH₂— 4-Ac—PhH Cl MeNH —CH₂— 3-Ac—Ph H Cl MeNH —CH₂— 2-Ac—Ph H Cl MeNH —CH₂— 4-MeO—PhH Cl MeNH —CH₂— 3-MeO—Ph H Cl MeNH —CH₂— 2-MeO—Ph H Cl MeNH —CH₂—4-i-PrO—Ph H Cl MeNH —CH₂— 3-i-PrO—Ph H Cl MeNH —CH₂— 2-i-PrO—Ph H ClMeNH —CH₂— 4-Cl-benzyl H Cl MeNH —CH₂— 3-Cl-benzyl H Cl MeNH —CH₂—2-Cl-benzyl H Cl MeNH —CH₂— 4-Br-benzyl H Cl MeNH —CH₂— 3-Br-benzyl H ClMeNH —CH₂— 2-Br-benzyl H Cl MeNH —CH₂— 4-Et-benzyl H Cl MeNH —CH₂—3-Et-benzyl H Cl MeNH —CH₂— 2-Et-benzyl H Cl MeNH —CH₂— 4-CN-benzyl H ClMeNH —CH₂— 3-CN-benzyl H Cl MeNH —CH₂— 2-CN-benzyl H Cl MeNH —CH₂—4-CF₃-benzyl H Cl MeNH —CH₂— 3-CF₃-benzyl H Cl MeNH —CH₂— 2-CF₃-benzyl HCl MeNH —CH₂— 4-CHF₂-benzyl H Cl MeNH —CH₂— 3-CHF₂-benzyl H Cl MeNH—CH₂— 2-CHF₂-benzyl H Cl MeNH —CH₂— 4-Ac-benzyl H Cl MeNH —CH₂—3-Ac-benzyl H Cl MeNH —CH₂— 2-Ac-benzyl H Cl MeNH —CH₂— 4-MeO-benzyl HCl MeNH —CH₂— 3-MeO-benzyl H Cl MeNH —CH₂— 2-MeO-benzyl H Cl MeNH —CH₂—4-i-PrO-benzyl H Cl MeNH —CH₂— 3-i-PrO-benzyl H Cl MeNH —CH₂—2-i-PrO-benzyl H Cl MeO —CH₂— 4-F—Ph H Cl MeO —CH₂— 3-F—Ph H Cl MeO—CH₂— 2-F—Ph H Cl MeO —CH₂— 4-Me—Ph H Cl MeO —CH₂— 3-Me—Ph H Cl MeO—CH₂— 2-Me—Ph H Cl MeO —CH₂— 4-i-Pr—Ph H Cl MeO —CH₂— 3-i-Pr—Ph H Cl MeO—CH₂— 2-i-Pr—Ph H Cl MeO —CH₂— 4-c-Pr—Ph H Cl MeO —CH₂— 3-c-Pr—Ph H ClMeO —CH₂— 2-c-Pr—Ph H Cl MeO —CH₂— 4-CF₃O—Ph H Cl MeO —CH₂— 3-CF₃O—Ph HCl MeO —CH₂— 2-CF₃O—Ph H Cl MeO —CH₂— 2-(CF₃C═O)—Ph H Cl MeO —CH₂—3-(CF₃C═O)—Ph H Cl MeO —CH₂— 4-(CF₃C═O)—Ph H Cl MeO —CH₂— 4-EtO—Ph H ClMeO —CH₂— 3-EtO—Ph H Cl MeO —CH₂— 2-EtO—Ph H Cl MeO —CH₂— 4-NO₂—Ph H ClMeO —CH₂— 3-NO₂—Ph H Cl MeO —CH₂— 2-NO₂—Ph H Cl MeO —CH₂— 4-(CO₂Me)—Ph HCl MeO —CH₂— 3-(CO₂Me)—Ph H Cl MeO —CH₂— 2-(CO₂Me)—Ph H Cl MeO —CH₂—4-Me(C═NMe)—Ph H Cl MeO —CH₂— 3-Me(C═NMe)—Ph H Cl MeO —CH₂—2-Me(C═NMe)—Ph H Cl MeO —CH₂— 4-Me(C═NOEt)—Ph H Cl MeO —CH₂—3-Me(C═NOEt)—Ph H Cl MeO —CH₂— 2-Me(C═NOEt)—Ph H Cl MeO —CH₂— 4-SiMe₃—PhH Cl MeO —CH₂— 3-SiMe₃—Ph H Cl MeO —CH₂— 2-SiMe₃—Ph H Cl MeO —CH₂—2,6-di-F—Ph H Cl MeO —CH₂— 2,5-di-F—Ph H Cl MeO —CH₂— 2,4-di-F—Ph H ClMeO —CH₂— 3,3-di-F—Ph H Cl MeO —CH₂— 3,4-di-F—Ph H Cl MeO —CH₂—2,6-di-CF₃—Ph H Cl MeO —CH₂— 2,5-di-CF₃—Ph H Cl MeO —CH₂— 2,4-di-CF₃—PhH Cl MeO —CH₂— 3,3-di-CF₃—Ph H Cl MeO —CH₂— 3,4-di-CF₃—Ph H Cl MeO —CH₂—2,6-di-MeO—Ph H Cl MeO —CH₂— 2,5-di-MeO—Ph H Cl MeO —CH₂— 2,4-di-MeO—PhH Cl MeO —CH₂— 3,3-di-MeO—Ph H Cl MeO —CH₂— 3,4-di-MeO—Ph H Cl MeO —CH₂—4-CF₂O—Ph H Cl MeO —CH₂— 3-CF₂O—Ph H Cl MeO —CH₂— 2-CF₂O—Ph H Cl MeO—CH₂— 2-F-3-CF₃—Ph H Cl MeO —CH₂— 2-F-4-CF₃—Ph H Cl MeO —CH₂—2-F-5-CF₃—Ph H Cl MeO —CH₂— 2-F-6-CF₃—Ph H Cl MeO —CH₂— 3-F-2-CF₃—Ph HCl MeO —CH₂— 3-F-4-CF₃—Ph H Cl MeO —CH₂— 3-F-5-CF₃—Ph H Cl MeO —CH₂—3-F-6-CF₃—Ph H Cl MeO —CH₂— 4-F-3-CF₃—Ph H Cl MeO —CH₂— 4-F-2-CF₃—Ph HCl MeO —CH₂— pyrid-3-yl H Cl MeO —CH₂— 2,4,6-triazin-1-yl H Cl MeO —CH₂—2-CF₃-pyrid-3-yl H Cl MeO —CH₂— 4-CF₃-pyrid-3-yl H Cl MeO —CH₂—5-CF₃-pyrid-3-yl H Cl MeO —CH₂— 6-CF₃-pyrid-3-yl H Cl MeO —CH₂—2-Me-pyrid-4-yl H Cl MeO —CH₂— 3-Me-pyrid-4-yl H Cl MeO —CH₂—2-Me-pyrid-3-yl H Cl MeO —CH₂— 4-Me-pyrid-3-yl H Cl MeO —CH₂—5-Me-pyrid-3-yl H Cl MeO —CH₂— 6-Me-pyrid-3-yl H Cl MeO —CH₂—5-F-thien-2-yl H Cl MeO —CH₂— 4-F-thien-2-yl H Cl MeO —CH₂—3-F-thien-2-yl H Cl MeO —CH₂— 5-OCF₃-thien-2-yl H Cl MeO —CH₂—4-OCF₃-thien-2-yl H Cl MeO —CH₂— 3-OCF₃-thien-2-yl H Cl MeO —CH₂—5-F-thien-3-yl H Cl MeO —CH₂— 4-F-thien-3-yl H Cl MeO —CH₂—2-F-thien-3-yl H Cl MeO —CH₂— 5-OCF₃-thien-3-yl H Cl MeO —CH₂—4-OCF₃-thien-3-yl H Cl MeO —CH₂— 2-OCF₃-thien-3-yl H Cl MeO —CH₂—thien-3-yl H Cl MeO —CH₂— 4-F-benzyl H Cl MeO —CH₂— 3-F-benzyl H Cl MeO—CH₂— 2-F-benzyl H Cl MeO —CH₂— 4-Me-benzyl H Cl MeO —CH₂— 3-Me-benzyl HCl MeO —CH₂— 2-Me-benzyl H Cl MeO —CH₂— 4-i-Pr-benzyl H Cl MeO —CH₂—3-i-Pr-benzyl H Cl MeO —CH₂— 2-i-Pr-benzyl H Cl MeO —CH₂— 4-c-Pr-benzylH Cl MeO —CH₂— 3-c-Pr-benzyl H Cl MeO —CH₂— 2-c-Pr-benzyl H Cl MeO —CH₂—4-CF₃O-benzyl H Cl MeO —CH₂— 3-CF₃O-benzyl H Cl MeO —CH₂— 2-CF₃O-benzylH Cl MeO —CH₂— 4-CHF₂O-benzyl H Cl MeO —CH₂— 3-CHF₂O-benzyl H Cl MeO—CH₂— 2-CHF₂O-benzyl H Cl MeO —CH₂— 2-(CF₃C═O)-benzyl H Cl MeO —CH₂—3-(CF₃C═O)-benzyl H Cl MeO —CH₂— 5-(CF₃C═O)-benzyl H Cl MeO —CH₂—4-EtO-benzyl H Cl MeO —CH₂— 3-EtO-benzyl H Cl MeO —CH₂— 2-EtO-benzyl HCl MeO —CH₂— 4-NO₂-benzyl H Cl MeO —CH₂— 3-NO₂-benzyl H Cl MeO —CH₂—2-NO₂-benzyl H Cl MeO —CH₂— phenethyl H Cl MeO —CH₂— ethyl H Cl MeO—CH₂— n-butyl H Cl MeO —CH₂— i-butyl H Cl MeO —CH₂— c-butyl H Cl MeO—CH₂— s-butyl H Cl MeO —CH₂— n-hexyl H Cl MeO —CH₂— c-hexyl H Cl MeO—CH₂— 2-naphthyl H Cl MeO N 4-F—Ph H Cl MeO N 3-F—Ph H Cl MeO N 2-F—Ph HCl MeO N 4-Me—Ph H Cl MeO N 3-Me—Ph H Cl MeO N 2-Me—Ph H Cl MeO N4-i-Pr—Ph H Cl MeO N 3-i-Pr—Ph H Cl MeO N 2-i-Pr—Ph H Cl MeO N 4-c-Pr—PhH Cl MeO N 3-c-Pr—Ph H Cl MeO N 2-c-Pr—Ph H Cl MeO N 4-CF₃O—Ph H Cl MeON 3-CF₃O—Ph H Cl MeO N 2-CF₃O—Ph H Cl MeO N 2-(CF₃C═O)—Ph H Cl MeO N3-(CF₃C═O)—Ph H Cl MeO N 5-(CF₃C═O)—Ph H Cl MeO N 4-EtO—Ph H Cl MeO N3-EtO—Ph H Cl MeO N 2-EtO—Ph H Cl MeO N 4-NO₂—Ph H Cl MeO N 3-NO₂—Ph HCl MeO N 2-NO₂—Ph H Cl MeO N 4-F-benzyl H Cl MeO N 3-F-benzyl H Cl MeO N2-F-benzyl H Cl MeO N 4-Me-benzyl H Cl MeO N 3-Me-benzyl H Cl MeO N2-Me-benzyl H Cl MeO N 4-i-Pr-benzyl H Cl MeO N 3-i-Pr-benzyl H Cl MeO N2-i-Pr-benzyl H Cl MeO N 4-c-Pr-benzyl H Cl MeO N 3-c-Pr-benzyl H Cl MeON 2-c-Pr-benzyl H Cl MeO N 4-CF₃O-benzyl H Cl MeO N 3-CF₃O-benzyl H ClMeO N 2-CF₃O-benzyl H Cl MeO N 4-CHF₂O-benzyl H Cl MeO N 3-CHF₂O-benzylH Cl MeO N 2-CHF₂O-benzyl H Cl MeO N 2-(CF₃C═O)-benzyl H Cl MeO N3-(CF₃C═O)-benzyl H Cl MeO N 5-(CF₃C═O)-benzyl H Cl MeO N 4-EtO-benzyl HCl MeO N 3-EtO-benzyl H Cl MeO N 2-EtO-benzyl H Cl MeO N 4-NO₂-benzyl HCl MeO N 3-NO₂-benzyl H Cl MeO N 2-NO₂-benzyl H Cl MeO O 4-F—Ph H Cl MeOO 3-F—Ph H Cl MeO O 2-F—Ph H Cl MeO O 4-Me—Ph H Cl MeO O 3-Me—Ph H ClMeO O 2-Me—Ph H Cl MeO O 4-i-Pr—Ph H Cl MeO O 3-i-Pr—Ph H Cl MeO O2-i-Pr—Ph H Cl MeO O 4-c-Pr—Ph H Cl MeO O 3-c-Pr—Ph H Cl MeO O 2-c-Pr—PhH Cl MeO O 4-CF₃O—Ph H Cl MeO O 3-CF₃O—Ph H Cl MeO O 2-CF₃O—Ph H Cl MeOO 2-(CF₃C═O)—Ph H Cl MeO O 3-(CF₃C═O)—Ph H Cl MeO O 5-(CF₃C═O)—Ph H ClMeO O 4-EtO—Ph H Cl MeO O 3-EtO—Ph H Cl MeO O 2-EtO—Ph H Cl MeO O4-F-benzyl H Cl MeO O 3-F-benzyl H Cl MeO O 2-F-benzyl H Cl MeO O 4-Mebenzyl H Cl MeO O 3-Me benzyl H Cl MeO O 2-Me-benzyl H Cl MeO O4-i-Pr-benzyl H Cl MeO O 3-i-Pr-benzyl H Cl MeO O 2-i-Pr-benzyl H Cl MeOO 4-c-Pr-benzyl H Cl MeO O 3-c-Pr-benzyl H Cl MeO O 2-c-Pr-benzyl H ClMeO O 4-CF₃O-benzyl H Cl MeO O 3-CF₃O-benzyl H Cl MeO O 2-CF₃O-benzyl HCl MeO O 4-CHF₂O-benzyl H Cl MeO O 3-CHF₂O-benzyl H Cl MeO O2-CHF₂O-benzyl H Cl MeO O 2-(CF₃C═O)-benzyl H Cl MeO O 3-(CF₃C═O)-benzylH Cl MeO O 5-(CF₃C═O)-benzyl H Cl MeO O 4-EtO-benzyl H Cl MeO O3-EtO-benzyl H Cl MeO O 2-EtO-benzyl H Cl MeO O 4-I-benzyl H Cl MeO O3-I-benzyl H Cl MeO O 2-I-benzyl H Me MeO —CH₂— 4-F—Ph H Me MeO —CH₂—3-F—Ph H Me MeO —CH₂— 2-F—Ph H Me MeO —CH₂— 4-Me—Ph H Me MeO —CH₂—3-Me—Ph H Me MeO —CH₂— 2-Me—Ph H Me MeO —CH₂— 4-i-Pr—Ph H Me MeO —CH₂—3-i-Pr—Ph H Me MeO —CH₂— 2-i-Pr—Ph H Me MeO —CH₂— 4-c-Pr—Ph H Me MeO—CH₂— 3-c-Pr—Ph H Me MeO —CH₂— 2-c-Pr—Ph H Me MeO —CH₂— 4-CF₃O—Ph H MeMeO —CH₂— 3-CF₃O—Ph H Me MeO —CH₂— 2-CF₃O—Ph H Me MeO —CH₂—2-(CF₃C═O)—Ph H Me MeO —CH₂— 3-(CF₃C═O)—Ph H Me MeO —CH₂— 5-(CF₃C═O)—PhH Me MeO —CH₂— 4-EtO—Ph H Me MeO —CH₂— 3-EtO—Ph H Me MeO —CH₂— 2-EtO—PhH Me MeO —CH₂— 4-NO₂—Ph H Me MeO —CH₂— 3-NO₂—Ph H Me MeO —CH₂— 2-NO₂—PhH Me MeO —CH₂— 4-F-benzyl H Me MeO —CH₂— 3-F-benzyl H Me MeO —CH₂—2-F-benzyl H Me MeO —CH₂— 4-Me-benzyl H Me MeO —CH₂— 3-Me-benzyl H MeMeO —CH₂— 2-Me-benzyl H Me MeO —CH₂— 4-i-Pr-benzyl H Me MeO —CH₂—3-i-Pr-benzyl H Me MeO —CH₂— 2-i-Pr-benzyl H Me MeO —CH₂— 4-c-Pr-benzylH Me MeO —CH₂— 3-c-Pr-benzyl H Me MeO —CH₂— 2-c-Pr-benzyl H Me MeO —CH₂—4-CF₃O-benzyl H Me MeO —CH₂— 3-CF₃O-benzyl H Me MeO —CH₂— 2-CF₃O-benzylH Me MeO —CH₂— 4-CHF₂O-benzyl H Me MeO —CH₂— 3-CHF₂O-benzyl H Me MeO—CH₂— 2-CHF₂O-benzyl H Me MeO —CH₂— 2-(CF₃C═O)-benzyl H Me MeO —CH₂—3-(CF₃C═O)-benzyl H Me MeO —CH₂— 5-(CF₃C═O)-benzyl H Me MeO —CH₂—4-EtO-benzyl H Me MeO —CH₂— 3-EtO-benzyl H Me MeO —CH₂— 2-EtO-benzyl HMe MeO —CH₂— 4-NO₂-benzyl H Me MeO —CH₂— 3-NO₂-benzyl H Me MeO —CH₂—2-NO₂-benzyl H Cl MeO —CH₂— 4-F—Ph Me Cl MeO —CH₂— 3-F—Ph Me Cl MeO—CH₂— 2-F—Ph Me Cl MeO —CH₂— 4-Me—Ph Me Cl MeO —CH₂— 3-Me—Ph Me Cl MeO—CH₂— 2-Me—Ph Me Cl MeO —CH₂— 4-i-Pr—Ph Me Cl MeO —CH₂— 3-i-Pr—Ph Me ClMeO —CH₂— 2-i-Pr—Ph Me Cl MeO —CH₂— 4-c-Pr—Ph Me Cl MeO —CH₂— 3-c-Pr—PhMe Cl MeO —CH₂— 2-c-Pr—Ph Me Cl MeO —CH₂— 4-CF₃O—Ph Me Cl MeO —CH₂—3-CF₃O—Ph Me Cl MeO —CH₂— 2-CF₃O—Ph Me Cl MeO —CH₂— 2-(CF₃C═O)—Ph Me ClMeO —CH₂— 3-(CF₃C═O)—Ph Me Cl MeO —CH₂— 5-(CF₃C═O)—Ph Me Cl MeO —CH₂—4-EtO—Ph Me Cl MeO —CH₂— 3-EtO—Ph Me Cl MeO —CH₂— 2-EtO—Ph Me Cl MeO—CH₂— 4-NO₂—Ph Me Cl MeO —CH₂— 3-NO₂—Ph Me Cl MeO —CH₂— 2-NO₂—Ph Me ClMeO —CH₂— 4-F-benzyl H Cl MeO —CH₂— 3-F-benzyl H Cl MeO —CH₂— 2-F-benzylH Cl MeO —CH₂— 4-Me-benzyl H Cl MeO —CH₂— 3-Me-benzyl H Cl MeO —CH₂—2-Me-benzyl H Cl MeO —CH₂— 4-i-Pr-benzyl H Cl MeO —CH₂— 3-i-Pr-benzyl HCl MeO —CH₂— 2-i-Pr-benzyl H Cl MeO —CH₂— 4-c-Pr-benzyl H Cl MeO —CH₂—3-c-Pr-benzyl H Cl MeO —CH₂— 2-c-Pr-benzyl H Cl MeO —CH₂— 4-CF₃O-benzylH Cl MeO —CH₂— 3-CF₃O-benzyl H Cl MeO —CH₂— 2-CF₃O-benzyl H Cl MeO —CH₂—4-CHF₂O benzyl H Cl MeO —CH₂— 3-CHF₂O-benzyl H Cl MeO —CH₂—2-CHF₂O-benzyl H Cl MeO —CH₂— 2-(CF₃C═O)-benzyl H Cl MeO —CH₂—3-(CF₃C═O)-benzyl H Cl MeO —CH₂— 5-(CF₃C═O)-benzyl H Cl MeO —CH₂—4-EtO-benzyl H Cl MeO —CH₂— 3-EtO-benzyl H Cl MeO —CH₂— 2-EtO-benzyl HCl MeNH —CH₂— 4-NO₂-benzyl H Cl MeNH —CH₂— 3-NO₂-benzyl H Cl MeNH —CH₂—2-NO₂-benzyl H Cl MeNH —CH₂— 4-F—Ph H Cl MeNH —CH₂— 3-F—Ph H Cl MeNH—CH₂— 2-F—Ph H Cl MeNH —CH₂— 4-Me—Ph H Cl MeNH —CH₂— 3-Me—Ph H Cl MeNH—CH₂— 2-Me—Ph H Cl MeNH —CH₂— 4-i-Pr—Ph H Cl MeNH —CH₂— 3-i-Pr—Ph H ClMeNH —CH₂— 2-i-Pr—Ph H Cl MeNH —CH₂— 4-c-Pr—Ph H Cl MeNH —CH₂— 3-c-Pr—PhH Cl MeNH —CH₂— 2-c-Pr—Ph H Cl MeNH —CH₂— 4-CF₃O—Ph H Cl MeNH —CH₂—3-CF₃O—Ph H Cl MeNH —CH₂— 2-CF₃O—Ph H Cl MeNH —CH₂— 2-(CF₃C═O)—Ph H ClMeNH —CH₂— 3-(CF₃C═O)—Ph H Cl MeNH —CH₂— 5-(CF₃C═O)—Ph H Cl MeNH —CH₂—4-EtO—Ph H Cl MeNH —CH₂— 3-EtO—Ph H Cl MeNH —CH₂— 2-EtO—Ph H Cl MeNH—CH₂— 4-NO₂—Ph H Cl MeNH —CH₂— 3-NO₂—Ph H Cl MeNH —CH₂— 2-NO₂—Ph H ClMeNH —CH₂— 4-F benzyl H Cl MeNH —CH₂— 3-F-benzyl H Cl MeNH —CH₂—2-F-benzyl H Cl MeNH —CH₂— 4-Me-benzyl H Cl MeNH —CH₂— 3-Me-benzyl H ClMeNH —CH₂— 2-Me-benzyl H Cl MeNH —CH₂— 4-i-Pr-benzyl H Cl MeNH —CH₂—3-i-Pr-benzyl H Cl MeNH —CH₂— 2-i-Pr-benzyl H Cl MeNH —CH₂—4-c-Pr-benzyl H Cl MeNH —CH₂— 3-c-Pr-benzyl H Cl MeNH —CH₂—2-c-Pr-benzyl H Cl MeNH —CH₂— 4-CF₃O-benzyl H Cl MeNH —CH₂—3-CF₃O-benzyl H Cl MeNH —CH₂— 2-CF₃O-benzyl H Cl MeNH —CH₂—4-CHF₂O-benzyl H Cl MeNH —CH₂— 3-CHF₂O-benzyl H Cl MeNH —CH₂—2-CHF₂O-benzyl H Cl MeNH —CH₂— 2-(CF₃C═O)-benzyl H Cl MeNH —CH₂—3-(CF₃C═O)-benzyl H Cl MeNH —CH₂— 5-(CF₃C═O)-benzyl H Cl MeNH —CH₂—4-EtO-benzyl H Cl MeNH —CH₂— 3-EtO-benzyl H Cl MeNH —CH₂— 2-EtO-benzyl HCl MeNH —CH₂— 4-NO₂-benzyl H Cl MeNH —CH₂— 3-NO₂-benzyl H Cl MeNH —CH₂—2-NO₂-benzyl H

TABLE 6

R¹ R^(14a) R^(14b) Cl 4-Cl—Ph H Cl 3-Cl—Ph H Cl 2-Cl—Ph H Cl 4-Br—Ph HCl 3-Br—Ph H Cl 2-Br—Ph H Cl 4-Et—Ph H Cl 3-Et—Ph H Cl 2-Et—Ph H Cl4-CN—Ph H Cl 3-CN—Ph H Cl 2-CN—Ph H Cl 4-CF₃—Ph H Cl 3-CF₃—Ph H Cl2-CF₃—Ph H Cl 4-Ac—Ph H Cl 3-Ac—Ph H Cl 2-Ac—Ph H Cl 4-MeO—Ph H Cl3-MeO—Ph H Cl 2-MeO—Ph H Cl 4-i-PrO—Ph H Cl 3-i-PrO—Ph H Cl 2-i-PrO—Ph HCl 4-I—Ph H Cl 3-I—Ph H Cl 2-I—Ph H Cl 4-Me(C═NH)—Ph H Cl 3-Me(C═NH)—PhH Cl 2-Me(C═NH)—Ph H Cl 4-Me(C═NOMe)—Ph H Cl 3-Me(C═NOMe)—Ph H Cl2-Me(C═NOMe)—Ph H Cl 4-MeNH(C═O)—Ph H Cl 3-MeNH(C═O)—Ph H Cl2-MeNH(C═O)—Ph H Cl 2,6-di-Cl—Ph H Cl 2,5-di-Cl—Ph H Cl 2,4-di-Cl—Ph HCl 3,3-di-Cl—Ph H Cl 3,4-di-Cl—Ph H Cl 2,6-di-Me—Ph H Cl 2,5-di-Me—Ph HCl 2,4-di-Me—Ph H Cl 3,3-di-Me—Ph H Cl 3,4-di-Me—Ph H Cl 2,6-di-CF₃O—PhH Cl 2,5-di-CF₃O—Ph H Cl 2,4-di-CF₃O—Ph H Cl 3,3-di-CF₃O—Ph H Cl3,4-di-CF₃O—Ph H Cl 4-CHF₂—Ph H Cl 3-CHF₂—Ph H Cl 2-CHF₂—Ph H Cl2-F-3-Cl—Ph H Cl 2-F-4-Cl—Ph H Cl 2-F-5-Cl—Ph H Cl 2-F-6-Cl—Ph H Cl3-F-2-Cl—Ph H Cl 3-F-4-Cl—Ph H Cl 3-F-5-Cl—Ph H Cl 3-F-6-Cl—Ph H Cl4-F-3-Cl—Ph H Cl 4-F-2-Cl—Ph H Cl pyrid-2-yl H Cl pyrid-4-yl H Cl3-CF₃-pyrid-2-yl H Cl 4-CF₃-pyrid-2-yl H Cl 5-CF₃-pyrid-2-yl H Cl6-CF₃-pyrid-2-yl H Cl 2-CF₃-pyrid-4-yl H Cl 3-CF₃-pyrid-4-yl H Cl3-Me-pyrid-2-yl H Cl 4-Me-pyrid-2-yl H Cl 5-Me-pyrid-2-yl H Cl6-Me-pyrid-2-yl H Cl 5-Cl-thien-2-yl H Cl 4-Cl-thien-2-yl H Cl3-Cl-thien-2-yl H Cl 5-CF₃-thien-2-yl H Cl 4-CF₃-thien-2-yl H Cl3-CF₃-thien-2-yl H Cl 5-Cl-thien-3-yl H Cl 4-Cl-thien-3-yl H Cl2-Cl-thien-3-yl H Cl 5-CF₃-thien-3-yl H Cl 4-CF₃-thien-3-yl H Cl2-CF₃-thien-3-yl H Cl thien-2-yl H Cl 4-Cl-benzyl H Cl 3-Cl-benzyl H Cl2-Cl-benzyl H Cl 4-Br-benzyl H Cl 3-Br-benzyl H Cl 2-Br-benzyl H Cl4-Et-benzyl H Cl 3-Et-benzyl H Cl 2-Et-benzyl H Cl 4-CN-benzyl H Cl3-CN-benzyl H Cl 2-CN-benzyl H Cl 4-CF₃-benzyl H Cl 3-CF₃-benzyl H Cl2-CF₃-benzyl H Cl 4-CHF₂-benzyl H Cl 3-CHF₂-benzyl H Cl 2-CHF₂-benzyl HCl 4-Ac-benzyl H Cl 3-Ac-benzyl H Cl 2-Ac-benzyl H Cl 4-MeO-benzyl H Cl3-MeO-benzyl H Cl 2-MeO-benzyl H Cl 4-i-PrO-benzyl H Cl 3-i-PrO-benzyl HCl 2-i-PrO-benzyl H Cl benzyl H Cl methyl H Cl n-propyl H Cl i-propyl HCl c-propyl H Cl n-pentyl H Cl c-pentyl H Cl n-heptyl H Cl 1-naphthyl HMe 4-Cl—Ph H Me 3-Cl—Ph H Me 2-Cl—Ph H Me 4-Br—Ph H Me 3-Br—Ph H Me2-Br—Ph H Me 4-Et—Ph H Me 3-Et—Ph H Me 2-Et—Ph H Me 4-CN—Ph H Me 3-CN—PhH Me 2-CN—Ph H Me 4-CF₃—Ph H Me 3-CF₃—Ph H Me 2-CF₃—Ph H Me 4-Ac—Ph H Me3-Ac—Ph H Me 2-Ac—Ph H Me 4-MeO—Ph H Me 3-MeO—Ph H Me 2-MeO—Ph H Me4-i-PrO—Ph H Me 3-i-PrO—Ph H Me 2-i-PrO—Ph H Me 4-Cl-benzyl H Me3-Cl-benzyl H Me 2-Cl-benzyl H Me 4-Br-benzyl H Me 3-Br-benzyl H Me2-Br-benzyl H Me 4-Et-benzyl H Me 3-Et-benzyl H Me 2-Et-benzyl H Me4-CN-benzyl H Me 3-CN-benzyl H Me 2-CN-benzyl H Me 4-CF₃-benzyl H Me3-CF₃-benzyl H Me 2-CF₃-benzyl H Me 4-CHF₂-benzyl H Me 3-CHF₂-benzyl HMe 2-CHF₂-benzyl H Me 4-Ac-benzyl H Me 3-Ac-benzyl H Me 2-Ac-benzyl H Me4-MeO-benzyl H Me 3-MeO-benzyl H Me 2-MeO-benzyl H Me 4-i-PrO-benzyl HMe 3-i-PrO-benzyl H Me 2-i-PrO-benzyl H Me 4-Cl—Ph Me Me 3-Cl—Ph Me Me2-Cl—Ph Me Me 4-Br—Ph Me Me 3-Br—Ph Me Me 2-Br—Ph Me Me 4-Et—Ph Me Me3-Et—Ph Me Me 2-Et—Ph Me Me 4-CN—Ph Me Me 3-CN—Ph Me Me 2-CN—Ph Me Me4-CF₃—Ph Me Me 3-CF₃—Ph Me Me 2-CF₃—Ph Me Me 4-Ac—Ph Me Me 3-Ac—Ph Me Me2-Ac—Ph Me Me 4-MeO—Ph Me Me 3-MeO—Ph Me Me 2-MeO—Ph Me Me 4-i-PrO—Ph MeMe 3-i-PrO—Ph Me Me 2-i-PrO—Ph Me Me 4-Cl-benzyl Me Me 3-Cl-benzyl Me Me2-Cl-benzyl Me Me 4-Br-benzyl Me Me 3-Br-benzyl Me Me 2-Br-benzyl Me Me4-Et-benzyl Me Me 3-Et-benzyl Me Me 2-Et-benzyl Me Me 4-CN-benzyl Me Me3-CN-benzyl Me Me 2-CN-benzyl Me Me 4-CF₃-benzyl Me Me 3-CF₃-benzyl MeMe 2-CF₃-benzyl Me Me 4-CHF₂-benzyl Me Me 3-CHF₂-benzyl Me Me2-CHF₂-benzyl Me Me 4-Ac-benzyl Me Me 3-Ac-benzyl Me Me 2-Ac-benzyl MeMe 4-MeO-benzyl Me Me 3-MeO-benzyl Me Me 2-MeO-benzyl Me Me4-i-PrO-benzyl Me Me 3-i-PrO-benzyl Me Me 2-i-PrO-benzyl Me Cl 4-F—Ph HCl 3-F—Ph H Cl 2-F—Ph H Cl 4-Me—Ph H Cl 3-Me—Ph H Cl 2-Me—Ph H Cl4-i-Pr—Ph H Cl 3-i-Pr—Ph H Cl 2-i-Pr—Ph H Cl 4-c-Pr—Ph H Cl 3-c-Pr—Ph HCl 2-c-Pr—Ph H Cl 4-CF₃O—Ph H Cl 3-CF₃O—Ph H Cl 2-CF₃O—Ph H Cl2-(CF₃C═O)—Ph H Cl 3-(CF₃C═O)—Ph H Cl 4-(CF₃C═O)—Ph H Cl 4-EtO—Ph H Cl3-EtO—Ph H Cl 2-EtO—Ph H Cl 4-NO₂—Ph H Cl 3-NO₂—Ph H Cl 2-NO₂—Ph H Cl4-(CO₂Me)—Ph H Cl 3-(CO₂Me)—Ph H Cl 2-(CO₂Me)—Ph H Cl 4-Me(C═NMe)—Ph HCl 3-Me(C═NMe)—Ph H Cl 2-Me(C═NMe)—Ph H Cl 4-Me(C═NOEt)—Ph H Cl3-Me(C═NOEt)—Ph H Cl 2-Me(C═NOEt)—Ph H Cl 4-SiMe₃—Ph H Cl 3-SiMe₃—Ph HCl 2-SiMe₃—Ph H Cl 2,6-di-F—Ph H Cl 2,5-di-F—Ph H Cl 2,4-di-F—Ph H Cl3,3-di-F—Ph H Cl 3,4-di-F—Ph H Cl 2,6-di-CF₃—Ph H Cl 2,5-di-CF₃—Ph H Cl2,4-di-CF₃—Ph H Cl 3,3-di-CF₃—Ph H Cl 3,4-di-CF₃—Ph H Cl 2,6-di-MeO—Ph HCl 2,5-di-MeO—Ph H Cl 2,4-di-MeO—Ph H Cl 3,3-di-MeO—Ph H Cl3,4-di-MeO—Ph H Cl 4-CHF₂O—Ph H Cl 3-CHF₂O—Ph H Cl 2-CHF₂O—Ph H Cl2-F-3-CF₃—Ph H Cl 2-F-4-CF₃—Ph H Cl 2-F-5-CF₃—Ph H Cl 2-F-6-CF₃—Ph H Cl3-F-2-CF₃—Ph H Cl 3-F-4-CF₃—Ph H Cl 3-F-5-CF₃—Ph H Cl 3-F-6-CF₃—Ph H Cl4-F-3-CF₃—Ph H Cl 4-F-2-CF₃—Ph H Cl pyrid-3-yl H Cl triazin-1-yl H Cl2-CF₃-pyrid-3-yl H Cl 4-CF₃-pyrid-3-yl H Cl 5-CF₃-pyrid-3-yl H Cl6-CF₃-pyrid-3-yl H Cl 2-Me-pyrid-4-yl H Cl 3-Me-pyrid-4-yl H Cl2-Me-pyrid-3-yl H Cl 4-Me-pyrid-3-yl H Cl 5-Me-pyrid-3-yl H Cl6-Me-pyrid-3-yl H Cl 5-F-thien-2-yl H Cl 4-F-thien-2-yl H Cl3-F-thien-2-yl H Cl 5-OCF₃-thien-2-yl H Cl 4-OCF₃-thien-2-yl H Cl3-OCF₃-thien-2-yl H Cl 5-F-thien-3-yl H Cl 4-F-thien-3-yl H Cl2-F-thien-3-yl H Cl 5-OCF₃-thien-3-yl H Cl 4-OCF₃-thien-3-yl H Cl2-OCF₃-thien-3-yl H Cl thien-3-yl H Cl 4-F-benzyl H Cl 3-F-benzyl H Cl2-F-benzyl H Cl 4-Me-benzyl H Cl 3-Me-benzyl H Cl 2-Me-benzyl H Cl4-i-Pr-benzyl H Cl 3-i-Pr-benzyl H Cl 2-i-Pr-benzyl H Cl 4-c-Pr-benzyl HCl 3-c-Pr-benzyl H Cl 2-c-Pr-benzyl H Cl 4-CF₃O-benzyl H Cl3-CF₃O-benzyl H Cl 2-CF₃O-benzyl H Cl 4-CHF₂O-benzyl H Cl 3-CHF₂O-benzylH Cl 2-CHF₂O-benzyl H Cl 2-(CF₃C═O)-benzyl H Cl 3-(CF₃C═O)-benzyl H Cl5-(CF₃C═O)-benzyl H Cl 4-EtO-benzyl H Cl 3-EtO-benzyl H Cl 2-EtO-benzylH Cl 4-NO₂-benzyl H Cl 3-NO₂-benzyl H Cl 2-NO₂-benzyl H Cl phenethyl HCl ethyl H Cl n-butyl H Cl i-butyl H Cl c-butyl H Cl s-butyl H Cln-hexyl H Cl c-hexyl H Cl 2-naphthyl H Me 4-F—Ph H Me 3-F—Ph H Me 2-F—PhH Me 4-Me—Ph H Me 3-Me—Ph H Me 2-Me—Ph H Me 4-i-Pr—Ph H Me 3-i-Pr—Ph HMe 2-i-Pr—Ph H Me 4-c-Pr—Ph H Me 3-c-Pr—Ph H Me 2-c-Pr—Ph H Me 4-CF₃O—PhH Me 3-CF₃O—Ph H Me 2-CF₃O—Ph H Me 2-(CF₃C═O)—Ph H Me 3-(CFC₃═O)—Ph H Me4-(CF₃C═O)—Ph H Me 4-EtO—Ph H Me 3-EtO—Ph H Me 2-EtO—Ph H Me 4-NO₂—Ph HMe 3-NO₂—Ph H Me 2-NO₂—Ph H Me 4-F-benzyl H Me 3-F-benzyl H Me2-F-benzyl H Me 4-Me-benzyl H Me 3-Me-benzyl H Me 2-Me-benzyl H Me4-i-Pr-benzyl H Me 3-i-Pr-benzyl H Me 2-i-Pr-benzyl H Me 4-c-Pr-benzyl HMe 3-c-Pr-benzyl H Me 2-c-Pr-benzyl H Me 4-CF₃O-benzyl H Me3-CF₃O-benzyl H Me 2-CF₃O-benzyl H Me 4-CHF₂O-benzyl H Me 3-CHF₂O-benzylH Me 2-CHF₂O-benzyl H Me 2-(CF₃C═O)-benzyl H Me 3-(CF₃C═O)-benzyl H Me5-(CF₃C═O)-benzyl H Me 4-EtO-benzyl H Me 3-EtO-benzyl H Me 2-EtO-benzylH Me 4-NO₂-benzyl H Me 3-NO₂-benzyl H Me 2-NO₂-benzyl H Me 4-F—Ph Me Me3-F—Ph Me Me 2-F—Ph Me Me 4-Me—Ph Me Me 3-Me—Ph Me Me 2-Me—Ph Me Me4-i-Pr—Ph Me Me 3-i-Pr—Ph Me Me 2-i-Pr—Ph Me Me 4-c-Pr—Ph Me Me3-c-Pr—Ph Me Me 2-c-Pr—Ph Me Me 4-CF₃O—Ph Me Me 3-CF₃O—Ph Me Me2-CF₃O—Ph Me Me 2-(CF₃C═O)—Ph Me Me 3-(CF₃C═O)—Ph Me Me 4-(CF₃C═O)—Ph MeMe 4-EtO—Ph Me Me 3-EtO—Ph Me Me 2-EtO—Ph Me Me 4-NO₂—Ph Me Me 3-NO₂—PhMe Me 2-NO₂—Ph Me Me 4-F-benzyl Me Me 3-F-benzyl Me Me 2-F-benzyl Me Me4-Me-benzyl Me Me 3-Me-benzyl Me Me 2-Me-benzyl Me Me 4-i-Pr-benzyl MeMe 3-i-Pr-benzyl Me Me 2-i-Pr-benzyl Me Me 4-c-Pr-benzyl Me Me3-c-Pr-benzyl Me Me 2-c-Pr-benzyl Me Me 4-CF₃O-benzyl Me Me3-CF₃O-benzyl Me Me 2-CF₃O-benzyl Me Me 4-CHF₂O-benzyl Me Me3-CHF₂O-benzyl Me Me 2-CHF₂O-benzyl Me Me 2-(CF₃C═O)-benzyl Me Me3-(CF₃C═O)-benzyl Me Me 5-(CF₃C═O)-benzyl Me Me 4-EtO-benzyl Me Me3-EtO-benzyl Me Me 2-EtO-benzyl Me Me 4-NO₂-benzyl Me Me 3-NO₂-benzyl MeMe 2-NO₂-benzyl Me

TABLE 7

R¹ R^(14a) R^(14b) Cl 4-Cl—Ph H Cl 3-Cl—Ph H Cl 2-Cl—Ph H Cl 4-Br—Ph HCl 3-Br—Ph H Cl 2-Br—Ph H Cl 4-Et—Ph H Cl 3-Et—Ph H Cl 2-Et—Ph H Cl4-CN—Ph H Cl 3-CN—Ph H Cl 2-CN—Ph H Cl 4-CF₃—Ph H Cl 3-CF₃—Ph H Cl2-CF₃—Ph H Cl 4-Ac—Ph H Cl 3-Ac—Ph H Cl 2-Ac—Ph H Cl 4-MeO—Ph H Cl3-MeO—Ph H Cl 2-MeO—Ph H Cl 4-i-PrO—Ph H Cl 3-i-PrO—Ph H Cl 2-i-PrO—Ph HCl 4-I—Ph H Cl 3-I—Ph H Cl 2-I—Ph H Cl 4-Me(C═NH)—Ph H Cl 3-Me(C═NH)—PhH Cl 2-Me(C═NH)—Ph H Cl 4-Me(C═NOMe)—Ph H Cl 3-Me(C═NOMe)—Ph H Cl2-Me(C═NOMe)—Ph H Cl 4-MeNH(C═O)—Ph H Cl 3-MeNH(C═O)—Ph H Cl2-MeNH(C═O)—Ph H Cl 2,6-di-Cl—Ph H Cl 2,5-di-Cl—Ph H Cl 2,4-di-Cl—Ph HCl 3,3-di-Cl—Ph H Cl 3,4-di-Cl—Ph H Cl 2,6-di-Me—Ph H Cl 2,5-di-Me—Ph HCl 2,4-di-Me—Ph H Cl 3,3-di-Me—Ph H Cl 3,4-di-Me—Ph H Cl 2,6-di-CF₃O—PhH Cl 2,5-di-CF₃O—Ph H Cl 2,4-di-CF₃O—Ph H Cl 3,3-di-CF₃O—Ph H Cl3,4-di-CF₃O—Ph H Cl 4-CHF₂—Ph H Cl 3-CHF₂—Ph H Cl 2-CHF₂—Ph H Cl2-F-3-Cl—Ph H Cl 2-F-4-Cl—Ph H Cl 2-F-5-Cl—Ph H Cl 2-F-6-Cl—Ph H Cl3-F-2-Cl—Ph H Cl 3-F-4-Cl—Ph H Cl 3-F-5-Cl—Ph H Cl 3-F-6-Cl—Ph H Cl4-F-3-Cl—Ph H Cl 4-F-2-Cl—Ph H Cl pyrid-2-yl H Cl pyrid-4-yl H Cl3-CF₃-pyrid-2-yl H Cl 4-CF₃-pyrid-2-yl H Cl 5-CF₃-pyrid-2-yl H Cl6-CF₃-pyrid-2-yl H Cl 2-CF₃-pyrid-4-yl H Cl 3-CF₃-pyrid-4-yl H Cl3-Me-pyrid-2-yl H Cl 4-Me-pyrid-2-yl H Cl 5-Me-pyrid-2-yl H Cl6-Me-pyrid-2-yl H Cl 5-Cl-thien-2-yl H Cl 4-Cl-thien-2-yl H Cl3-Cl-thien-2-yl H Cl 5-CF₃-thien-2-yl H Cl 4-CF₃-thien-2-yl H Cl3-CF₃-thien-2-yl H Cl 5-Cl-thien-3-yl H Cl 4-Cl-thien-3-yl H Cl2-Cl-thien-3-yl H Cl 5-CF₃-thien-3-yl H Cl 4-CF₃-thien-3-yl H Cl2-CF₃-thien-3-yl H Cl thien-2-yl H Cl 4-Cl-benzyl H Cl 3-Cl-benzyl H Cl2-Cl-benzyl H Cl 4-Br-benzyl H Cl 3-Br-benzyl H Cl 2-Br-benzyl H Cl4-Et-benzyl H Cl 3-Et-benzyl H Cl 2-Et-benzyl H Cl 4-CN-benzyl H Cl3-CN-benzyl H Cl 2-CN-benzyl H Cl 4-CF₃-benzyl H Cl 3-CF₃-benzyl H Cl2-CF₃-benzyl H Cl 4-CHF₂-benzyl H Cl 3-CHF₂-benzyl H Cl 2-CHF₂-benzyl HCl 4-Ac-benzyl H Cl 3-Ac-benzyl H Cl 2-Ac-benzyl H Cl 4-MeO-benzyl H Cl3-MeO-benzyl H Cl 2-MeO-benzyl H Cl 4-i-PrO-benzyl H Cl 3-i-PrO-benzyl HCl 2-i-PrO-benzyl H Cl benzyl H Cl methyl H Cl n-propyl H Cl i-propyl HCl c-propyl H Cl n-pentyl H Cl c-pentyl H Cl n-heptyl H Cl 1-naphthyl HMe 4-Cl—Ph H Me 3-Cl—Ph H Me 2-Cl—Ph H Me 4-Br—Ph H Me 3-Br—Ph H Me2-Br—Ph H Me 4-Et—Ph H Me 3-Et—Ph H Me 2-Et—Ph H Me 4-CN—Ph H Me 3-CN—PhH Me 2-CN—Ph H Me 4-CF₃—Ph H Me 3-CF₃—Ph H Me 2-CF₃—Ph H Me 4-Ac—Ph H Me3-Ac—Ph H Me 2-Ac—Ph H Me 4-MeO—Ph H Me 3-MeO—Ph H Me 2-MeO—Ph H Me4-i-PrO—Ph H Me 3-i-PrO—Ph H Me 2-i-PrO—Ph H Me 4-Cl-benzyl H Me3-Cl-benzyl H Me 2-Cl-benzyl H Me 4-Br-benzyl H Me 3-Br-benzyl H Me2-Br-benzyl H Me 4-Et-benzyl H Me 3-Et-benzyl H Me 2-Et-benzyl H Me4-CN-benzyl H Me 3-CN-benzyl H Me 2-CN-benzyl H Me 4-CF₃-benzyl H Me3-CF₃-benzyl H Me 2-CF₃-benzyl H Me 4-CHF₂-benzyl H Me 3-CHF₂-benzyl HMe 2-CHF₂-benzyl H Me 4-Ac-benzyl H Me 3-Ac-benzyl H Me 2-Ac-benzyl H Me4-MeO-benzyl H Me 3-MeO-benzyl H Me 2-MeO-benzyl H Me 4-i-PrO-benzyl HMe 3-i-PrO-benzyl H Me 2-i-PrO-benzyl H Me 4-Cl—Ph Me Me 3-Cl—Ph Me Me2-Cl—Ph Me Me 4-Br—Ph Me Me 3-Br—Ph Me Me 2-Br—Ph Me Me 4-Et—Ph Me Me3-Et—Ph Me Me 2-Et—Ph Me Me 4-CN—Ph Me Me 3-CN—Ph Me Me 2-CN—Ph Me Me4-CF₃—Ph Me Me 3-CF₃—Ph Me Me 2-CF₃—Ph Me Me 4-Ac—Ph Me Me 3-Ac—Ph Me Me2-Ac—Ph Me Me 4-MeO—Ph Me Me 3-MeO—Ph Me Me 2-MeO—Ph Me Me 4-i-PrO—Ph MeMe 3-i-PrO—Ph Me Me 2-i-PrO—Ph Me Me 4-Cl-benzyl Me Me 3-Cl-benzyl Me Me2-Cl-benzyl Me Me 4-Br-benzyl Me Me 3-Br-benzyl Me Me 2-Br-benzyl Me Me4-Et-benzyl Me Me 3-Et-benzyl Me Me 2-Et-benzyl Me Me 4-CN-benzyl Me Me3-CN-benzyl Me Me 2-CN-benzyl Me Me 4-CF₃-benzyl Me Me 3-CF₃-benzyl MeMe 2-CF₃-benzyl Me Me 4-CHF₂-benzyl Me Me 3-CHF₂-benzyl Me Me2-CHF₂-benzyl Me Me 4-Ac-benzyl Me Me 3-Ac-benzyl Me Me 2-Ac-benzyl MeMe 4-MeO-benzyl Me Me 3-MeO-benzyl Me Me 2-MeO-benzyl Me Me4-i-PrO-benzyl Me Me 3-i-PrO-benzyl Me Me 2-i-PrO-benzyl Me Cl 4-F—Ph HCl 3-F—Ph H Cl 2-F—Ph H Cl 4-Me—Ph H Cl 3-Me—Ph H Cl 2-Me—Ph H Cl4-i-Pr—Ph H Cl 3-i-Pr—Ph H Cl 2-i-Pr—Ph H Cl 4-c-Pr—Ph H Cl 3-c-Pr—Ph HCl 2-c-Pr—Ph H Cl 4-CF₃O—Ph H Cl 3-CF₃O—Ph H Cl 2-CF₃O—Ph H Cl2-(CF₃C═O)—Ph H Cl 3-(CF₃C═O)—Ph H Cl 4-(CF₃C═O)—Ph H Cl 4-EtO—Ph H Cl3-EtO—Ph H Cl 2-EtO—Ph H Cl 4-NO₂—Ph H Cl 3-NO₂—Ph H Cl 2-NO₂—Ph H Cl4-(CO₂Me)—Ph H Cl 3-(CO₂Me)—Ph H Cl 2-(CO₂Me)—Ph H Cl 4-Me(C═NMe)—Ph HCl 3-Me(C═NMe)—Ph H Cl 2-Me(C═NMe)—Ph H Cl 4-Me(C═NOEt)—Ph H Cl3-Me(C═NOEt)—Ph H Cl 2-Me(C═NOEt)—Ph H Cl 4-SiMe₃—Ph H Cl 3-SiMe₃—Ph HCl 2-SiMe₃—Ph H Cl 2,6-di-F—Ph H Cl 2,5-di-F—Ph H Cl 2,4-di-F—Ph H Cl3,3-di-F—Ph H Cl 3,4-di-F—Ph H Cl 2,6-di-CF₃—Ph H Cl 2,5-di-CF₃—Ph H Cl2,4-di-CF₃—Ph H Cl 3,3-di-CF₃—Ph H Cl 3,4-di-CF₃—Ph H Cl 2,6-di-MeO—Ph HCl 2,5-di-MeO—Ph H Cl 2,4-di-MeO—Ph H Cl 3,3-di-MeO—Ph H Cl3,4-di-MeO—Ph H Cl 4-CHF₂O—Ph H Cl 3-CHF₂O—Ph H Cl 2-CHF₂O—Ph H Cl2-F-3-CF₃—Ph H Cl 2-F-4-CF₃—Ph H Cl 2-F-5-CF₃—Ph H Cl 2-F-6-CF₃—Ph H Cl3-F-2-CF₃—Ph H Cl 3-F-4-CF₃—Ph H Cl 3-F-5-CF₃—Ph H Cl 3-F-6-CF₃—Ph H Cl4-F-3-CF₃—Ph H Cl 4-F-2-CF₃—Ph H Cl pyrid-3-yl H Cl triazin-1-yl H Cl2-CF₃-pyrid-3-yl H Cl 4-CF₃-pyrid-3-yl H Cl 5-CF₃-pyrid-3-yl H Cl6-CF₃-pyrid-3-yl H Cl 2-Me-pyrid-4-yl H Cl 3-Me-pyrid-4-yl H Cl2-Me-pyrid-3-yl H Cl 4-Me-pyrid-3-yl H Cl 5-Me-pyrid-3-yl H Cl6-Me-pyrid-3-yl H Cl 5-F-thien-2-yl H Cl 4-F-thien-2-yl H Cl3-F-thien-2-yl H Cl 5-OCF₃-thien-2-yl H Cl 4-OCF₃-thien-2-yl H Cl3-OCF₃-thien-2-yl H Cl 5-F-thien-3-yl H Cl 4-F-thien-3-yl H Cl2-F-thien-3-yl H Cl 5-OCF₃-thien-3-yl H Cl 4-OCF₃-thien-3-yl H Cl2-OCF₃-thien-3-yl H Cl thien-3-yl H Cl 4-F-benzyl H Cl 3-F-benzyl H Cl2-F-benzyl H Cl 4-Me-benzyl H Cl 3-Me-benzyl H Cl 2-Me-benzyl H Cl4-i-Pr-benzyl H Cl 3-i-Pr-benzyl H Cl 2-i-Pr-benzyl H Cl 4-c-Pr-benzyl HCl 3-c-Pr-benzyl H Cl 2-c-Pr-benzyl H Cl 4-CF₃O-benzyl H Cl3-CF₃O-benzyl H Cl 2-CF₃O-benzyl H Cl 4-CHF₂O-benzyl H Cl 3-CHF₂O-benzylH Cl 2-CHF₂O-benzyl H Cl 2-(CF₃C═O)-benzyl H Cl 3-(CF₃C═O)-benzyl H Cl5-(CF₃C═O)-benzyl H Cl 4-EtO-benzyl H Cl 3-EtO-benzyl H Cl 2-EtO-benzylH Cl 4-NO₂-benzyl H Cl 3-NO₂-benzyl H Cl 2-NO₂-benzyl H Cl phenethyl HCl ethyl H Cl n-butyl H Cl i-butyl H Cl c-butyl H Cl s-butyl H Cln-hexyl H Cl c-hexyl H Cl 2-naphthyl H Me 4-F—Ph H Me 3-F—Ph H Me 2-F—PhH Me 4-Me—Ph H Me 3-Me—Ph H Me 2-Me—Ph H Me 4-i-Pr—Ph H Me 3-i-Pr—Ph HMe 2-i-Pr—Ph H Me 4-c-Pr—Ph H Me 3-c-Pr—Ph H Me 2-c-Pr—Ph H Me 4-CF₃O—PhH Me 3-CF₃O—Ph H Me 2-CF₃O—Ph H Me 2-(CF₃C═O)—Ph H Me 3-(CF₃C═O)—Ph H Me4-(CF₃C═O)—Ph H Me 4-EtO—Ph H Me 3-EtO—Ph H Me 2-EtO—Ph H Me 4-NO₂—Ph HMe 3-NO₂—Ph H Me 2-NO₂—Ph H Me 4-F-benzyl H Me 3-F-benzyl H Me2-F-benzyl H Me 4-Me-benzyl H Me 3-Me-benzyl H Me 2-Me-benzyl H Me4-i-Pr-benzyl H Me 3-i-Pr-benzyl H Me 2-i-Pr-benzyl H Me 4-c-Pr-benzyl HMe 3-c-Pr-benzyl H Me 2-c-Pr-benzyl H Me 4-CF₃O-benzyl H Me3-CF₃O-benzyl H Me 2-CF₃O-benzyl H Me 4-CHF₂O-benzyl H Me 3-CHF₂O-benzylH Me 2-CHF₂O-benzyl H Me 2-(CF₃C═O)-benzyl H Me 3-(CF₃C═O)-benzyl H Me5-(CF₃C═O)-benzyl H Me 4-EtO-benzyl H Me 3-EtO-benzyl H Me 2-EtO-benzylH Me 4-NO₂-benzyl H Me 3-NO₂-benzyl H Me 2-NO₂-benzyl H Me 4-F—Ph Me Me3-F—Ph Me Me 2-F—Ph Me Me 4-Me—Ph Me Me 3-Me—Ph Me Me 2-Me—Ph Me Me4-i-Pr—Ph Me Me 3-i-Pr—Ph Me Me 2-i-Pr—Ph Me Me 4-c-Pr—Ph Me Me3-c-Pr—Ph Me Me 2-c-Pr—Ph Me Me 4-CF₃O—Ph Me Me 3-CF₃O—Ph Me Me2-CF₃O—Ph Me Me 2-(CF₃C═O)—Ph Me Me 3-(CF₃C═O)—Ph Me Me 4-(CF₃C═O)—Ph MeMe 4-EtO—Ph Me Me 3-EtO—Ph Me Me 2-EtO—Ph Me Me 4-NO₂—Ph Me Me 3-NO₂—PhMe Me 2-NO₂—Ph Me Me 4-F-benzyl Me Me 3-F-benzyl Me Me 2-F-benzyl Me Me4-Me-benzyl Me Me 3-Me-benzyl Me Me 2-Me-benzyl Me Me 4-i-Pr-benzyl MeMe 3-i-Pr-benzyl Me Me 2-i-Pr-benzyl Me Me 4-c-Pr-benzyl Me Me3-c-Pr-benzyl Me Me 2-c-Pr-benzyl Me Me 4-CF₃O-benzyl Me Me3-CF₃O-benzyl Me Me 2-CF₃O-benzyl Me Me 4-CHF₂O-benzyl Me Me3-CHF₂O-benzyl Me Me 2-CHF₂O-benzyl Me Me 2-(CF₃C═O)-benzyl Me Me3-(CF₃C═O)-benzyl Me Me 5-(CF₃C═O)-benzyl Me Me 4-EtO-benzyl Me Me3-EtO-benzyl Me Me 2-EtO-benzyl Me Me 4-NO₂-benzyl Me Me 3-NO₂-benzyl MeMe 2-NO₂-benzyl Me

TABLE 8

R¹ R¹⁴ Cl 4-Cl—Ph Cl 3-Cl—Ph Cl 2-Cl—Ph Cl 4-Br—Ph Cl 3-Br—Ph Cl 2-Br—PhCl 4-Et—Ph Cl 3-Et—Ph Cl 2-Et—Ph Cl 4-CN—Ph Cl 3-CN—Ph Cl 2-CN—Ph Cl4-CF₃—Ph Cl 3-CF₃—Ph Cl 2-CF₃—Ph Cl 4-Ac—Ph Cl 3-Ac—Ph Cl 2-Ac—Ph Cl4-MeO—Ph Cl 3-MeO—Ph Cl 2-MeO—Ph Cl 4-i-PrO—Ph Cl 3-i-PrO—Ph Cl2-i-PrO—Ph Cl 4-I—Ph Cl 3-I—Ph Cl 2-I—Ph Cl 4-Me(C═NH)—Ph Cl3-Me(C═NH)—Ph Cl 2-Me(C═NH)—Ph Cl 4-Me(C═NOMe)—Ph Cl 3-Me(C═NOMe)—Ph Cl2-Me(C═NOMe)—Ph Cl 4-MeNH(C═O)—Ph Cl 3-MeNH(C═O)—Ph Cl 2-MeNH(C═O)—Ph Cl2,6-di-Cl—Ph Cl 2,5-di-Cl—Ph Cl 2,4-di-Cl—Ph Cl 3,3-di-Cl—Ph Cl3,4-di-Cl—Ph Cl 2,6-di-Me—Ph Cl 2,5-di-Me—Ph Cl 2,4-di-Me—Ph Cl3,3-di-Me—Ph Cl 3,4-di-Me—Ph Cl 2,6-di-CF₃O—Ph Cl 2,5-di-CF₃O—Ph Cl2,4-di-CF₃O—Ph Cl 3,3-di-CF₃O—Ph Cl 3,4-di-CF₃O—Ph Cl 4-CHF₂—Ph Cl3-CHF₂—Ph Cl 2-CHF₂—Ph Cl 2-F-3-Cl—Ph Cl 2-F-4-Cl—Ph Cl 2-F-5-Cl—Ph Cl2-F-6-Cl—Ph Cl 3-F-2-Cl—Ph Cl 3-F-4-Cl—Ph Cl 3-F-5-Cl—Ph Cl 3-F-6-Cl—PhCl 4-F-3-Cl—Ph Cl 4-F-2-Cl—Ph Cl pyrid-2-yl Cl pyrid-4-yl Cl3-CF₃-pyrid-2-yl Cl 4-CF₃-pyrid-2-yl Cl 5-CF₃-pyrid-2-yl Cl6-CF₃-pyrid-2-yl Cl 2-CF₃-pyrid-4-yl Cl 3-CF₃-pyrid-4-yl Cl3-Me-pyrid-2-yl Cl 4-Me-pyrid-2-yl Cl 5-Me-pyrid-2-yl Cl 6-Me-pyrid-2-ylCl 5-Cl-thien-2-yl Cl 4-Cl-thien-2-yl Cl 3-Cl-thien-2-yl Cl5-CF₃-thien-2-yl Cl 4-CF₃-thien-2-yl Cl 3-CF₃-thien-2-yl Cl5-Cl-thien-3-yl Cl 4-Cl-thien-3-yl Cl 2-Cl-thien-3-yl Cl5-CF₃-thien-3-yl Cl 4-CF₃-thien-3-yl Cl 2-CF₃-thien-3-yl Cl thien-2-ylCl 4-Cl-benzyl Cl 3-Cl-benzyl Cl 2-Cl-benzyl Cl 4-Br-benzyl Cl3-Br-benzyl Cl 2-Br-benzyl Cl 4-Et-benzyl Cl 3-Et-benzyl Cl 2-Et-benzylCl 4-CN-benzyl Cl 3-CN-benzyl Cl 2-CN-benzyl Cl 4-CF₃-benzyl Cl3-CF₃-benzyl Cl 2-CF₃-benzyl Cl 4-CHF₂-benzyl Cl 3-CHF₂-benzyl Cl2-CHF₂-benzyl Cl 4-Ac-benzyl Cl 3-Ac-benzyl Cl 2-Ac-benzyl Cl4-MeO-benzyl Cl 3-MeO-benzyl Cl 2-MeO-benzyl Cl 4-i-PrO-benzyl Cl3-i-PrO-benzyl Cl 2-i-PrO-benzyl Cl benzyl Cl methyl Cl n-propyl Cli-propyl Cl c-propyl Cl n-pentyl Cl c-pentyl Cl n-heptyl Cl 1-naphthylMe 4-Cl—Ph Me 3-Cl—Ph Me 2-Cl—Ph Me 4-Br—Ph Me 3-Br—Ph Me 2-Br—Ph Me4-Et—Ph Me 3-Et—Ph Me 2-Et—Ph Me 4-CN—Ph Me 3-CN—Ph Me 2-CN—Ph Me4-CF₃—Ph Me 3-CF₃—Ph Me 2-CF₃—Ph Me 4-Ac—Ph Me 3-Ac—Ph Me 2-Ac—Ph Me4-MeO—Ph Me 3-MeO—Ph Me 2-MeO—Ph Me 4-i-PrO—Ph Me 3-i-PrO—Ph Me2-i-PrO—Ph Me 4-Cl-benzyl Me 3-Cl-benzyl Me 2-Cl-benzyl Me 4-Br-benzylMe 3-Br-benzyl Me 2-Br-benzyl Me 4-Et-benzyl Me 3-Et-benzyl Me2-Et-benzyl Me 4-CN-benzyl Me 3-CN-benzyl Me 2-CN-benzyl Me 4-CF₃-benzylMe 3-CF₃-benzyl Me 2-CF₃-benzyl Me 4-CHF₂-benzyl Me 3-CHF₂-benzyl Me2-CHF₂-benzyl Me 4-Ac-benzyl Me 3-Ac-benzyl Me 2-Ac-benzyl Me4-MeO-benzyl Me 3-MeO-benzyl Me 2-MeO-benzyl Me 4-i-PrO-benzyl Me3-i-PrO-benzyl Me 2-i-PrO-benzyl Cl 4-F—Ph Cl 3-F—Ph Cl 2-F—Ph Cl4-Me—Ph Cl 3-Me—Ph Cl 2-Me—Ph Cl 4-i-Pr—Ph Cl 3-i-Pr—Ph Cl 2-i-Pr—Ph Cl4-c-Pr—Ph Cl 3-c-Pr—Ph Cl 2-c-Pr—Ph Cl 4-CF₃O—Ph Cl 3-CF₃O—Ph Cl2-CF₃O—Ph Cl 2-(CF₃C═O)—Ph Cl 3-(CF₃C═O)—Ph Cl 4-(CF₃C═O)—Ph Cl 4-EtO—PhCl 3-EtO—Ph Cl 2-EtO—Ph Cl 4-NO₂—Ph Cl 3-NO₂—Ph Cl 2-NO₂—Ph Cl4-(CO₂Me)—Ph Cl 3-(CO₂Me)—Ph Cl 2-(CO₂Me)—Ph Cl 4-Me(C═NMe)—Ph Cl3-Me(C═NMe)—Ph Cl 2-Me(C═NMe)—Ph Cl 4-Me(C═NOEt)—Ph Cl 3-Me(C═NOEt)—PhCl 2-Me(C═NOEt)—Ph Cl 4-SiMe₃—Ph Cl 3-SiMe₃—Ph Cl 2-SiMe₃—Ph Cl2,6-di-F—Ph Cl 2,5-di-F—Ph Cl 2,4-di-F—Ph Cl 3,3-di-F—Ph Cl 3,4-di-F—PhCl 2,6-di-CF₃—Ph Cl 2,5-di-CF₃—Ph Cl 2,4-di-CF₃—Ph Cl 3,3-di-CF₃—Ph Cl3,4-di-CF₃—Ph Cl 2,6-di-MeO—Ph Cl 2,5-di-MeO—Ph Cl 2,4-di-MeO—Ph Cl3,3-di-MeO—Ph Cl 3,4-di-MeO—Ph Cl 4-CHF₂O—Ph Cl 3-CHF₂O—Ph Cl 2-CHF₂O—PhCl 2-F-3-CF₃—Ph Cl 2-F-4-CF₃—Ph Cl 2-F-5-CF₃—Ph Cl 2-F-6-CF₃—Ph Cl3-F-2-CF₃—Ph Cl 3-F-4-CF₃—Ph Cl 3-F-5-CF₃—Ph Cl 3-F-6-CF₃—Ph Cl4-F-3-CF₃—Ph Cl 4-F-2-CF₃—Ph Cl pyrid-3-yl Cl 2,4,6-triazin-1-yl Cl2-CF₃-pyrid-3-yl Cl 4-CF₃-pyrid-3-yl Cl 5-CF₃-pyrid-3-yl Cl6-CF₃-pyrid-3-yl Cl 2-Me-pyrid-4-yl Cl 3-Me-pyrid-4-yl Cl2-Me-pyrid-3-yl Cl 4-Me-pyrid-3-yl Cl 5-Me-pyrid-3-yl Cl 6-Me-pyrid-3-ylCl 5-F-thien-2-yl Cl 4-F-thien-2-yl Cl 3-F-thien-2-yl Cl5-OCF₃-thien-2-yl Cl 4-OCF₃-thien-2-yl Cl 3-OCF₃-thien-2-yl Cl5-F-thien-3-yl Cl 4-F-thien-3-yl Cl 2-F-thien-3-yl Cl 5-OCF₃-thien-3-ylCl 4-OCF₃-thien-3-yl Cl 2-OCF₃-thien-3-yl Cl thien-3-yl Cl 4-F-benzyl Cl3-F-benzyl Cl 2-F-benzyl Cl 4-Me-benzyl Cl 3-Me-benzyl Cl 2-Me-benzyl Cl4-i-Pr-benzyl Cl 3-i-Pr-benzyl Cl 2-i-Pr-benzyl Cl 4-c-Pr-benzyl Cl3-c-Pr-benzyl Cl 2-c-Pr-benzyl Cl 4-CF₃O-benzyl Cl 3-CF₃O-benzyl Cl2-CF₃O-benzyl Cl 4-CHF₂O-benzyl Cl 3-CHF₂O-benzyl Cl 2-CHF₂O-benzyl Cl2-(CF₃C═O)-benzyl Cl 3-(CF₃C═O)-benzyl Cl 5-(CF₃C═O)-benzyl Cl4-EtO-benzyl Cl 3-EtO-benzyl Cl 2-EtO-benzyl Cl 4-NO₂-benzyl Cl3-NO₂-benzyl Cl 2-NO₂-benzyl Cl phenethyl Cl ethyl Cl n-butyl Cl i-butylCl c-butyl Cl s-butyl Cl n-hexyl Cl c-hexyl Cl 2-naphthyl Me 4-F—Ph Me3-F—Ph Me 2-F—Ph Me 4-Me—Ph Me 3-Me—Ph Me 2-Me—Ph Me 4-i-Pr—Ph Me3-i-Pr—Ph Me 2-i-Pr—Ph Me 4-c-Pr—Ph Me 3-c-Pr—Ph Me 2-c-Pr—Ph Me4-CF₃O—Ph Me 3-CF₃O—Ph Me 2-CF₃O—Ph Me 2-(CF₃C═O)—Ph Me 3-(CF₃C═O)—Ph Me4-(CF₃C═O)—Ph Me 4-EtO—Ph Me 3-EtO—Ph Me 2-EtO—Ph Me 4-NO₂—Ph Me3-NO₂—Ph Me 2-NO₂—Ph Me 4-F-benzyl Me 3-F-benzyl Me 2-F-benzyl Me4-Me-benzyl Me 3-Me-benzyl Me 2-Me-benzyl Me 4-i-Pr-benzyl Me3-i-Pr-benzyl Me 2-i-Pr-benzyl Me 4-c-Pr-benzyl Me 3-c-Pr-benzyl Me2-c-Pr-benzyl Me 4-CF₃O-benzyl Me 3-CF₃O-benzyl Me 2-CF₃O-benzyl Me4-CHF₂O-benzyl Me 3-CHF₂O-benzyl Me 2-CHF₂O-benzyl Me 2-(CF₃C═O)-benzylMe 3-(CF₃C═O)-benzyl Me 5-(CF₃C═O)-benzyl Me 4-EtO-benzyl Me3-EtO-benzyl Me 2-EtO-benzyl Me 4-NO₂-benzyl Me 3-NO₂-benzyl Me2-NO₂-benzyl

TABLE 9

R¹ R^(14a) R^(14b) Cl Me H Cl n-propyl H Cl n-butyl H Cl n-pentyl H Cln-hexyl H Cl Ph H Cl i-propyl H Cl s-butyl H Cl CF₃ H Cl CF₃CH₂ H Me MeH Me n-propyl H Me n-butyl H Me n-pentyl H Me n-hexyl H Me Ph H Mei-propyl H Me s-butyl H Me CF₃ H Me CF₃CH₂ H Cl Me Me Cl n-propyl Me Cln-butyl Me Cl n-pentyl Me Cl n-hexyl Me Cl Ph Me Cl i-propyl Me Cls-butyl Me Cl CF₃ Me Cl CF₃CH₂ Me Cl Me CF₃ Cl n-propyl CF₃ Cl n-butylCF₃ Cl n-pentyl CF₃ Cl n-hexyl CF₃ Cl Ph CF₃ Cl i-propyl CF₃ Cl s-butylCF₃ Cl CF₃ CF₃ Cl CF₃CH₂ CF₃ Cl Et H Cl c-propyl H Cl c-butyl H Clc-pentyl H Cl c-hexyl H Cl benzyl H Cl i-butyl H Cl t-butyl H Cl CHF₂ HCl CF₂CH₂ H Me Et H Me c-propyl H Me c-butyl H Me c-pentyl H Me c-hexylH Me benzyl H Me i-butyl H Me t-butyl H Me CHF₂ H Me CF₂CH₂ H Cl Et MeCl c-propyl Me Cl c-butyl Me Cl c-pentyl Me Cl c-hexyl Me Cl benzyl MeCl i-butyl Me Cl t-butyl Me Cl CHF₂ Me Cl CF₂CH₂ Me Cl Et CF₃ Clc-propyl CF₃ Cl c-butyl CF₃ Cl c-pentyl CF₃ Cl c-hexyl CF₃ Cl benzyl CF₃Cl i-butyl CF₃ Cl t-butyl CF₃ Cl CHF₂ CF₃ Cl CF₂CH₂ CF₃

TABLE 10

R¹ R¹⁴ Cl 4-Cl—Ph Cl 3-Cl—Ph Cl 2-Cl—Ph Cl 4-Br—Ph Cl 3-Br—Ph Cl 2-Br—PhCl 4-Et—Ph Cl 3-Et—Ph Cl 2-Et—Ph Cl 4-CN—Ph Cl 3-CN—Ph Cl 2-CN—Ph Cl4-CF₃—Ph Cl 3-CF₃—Ph Cl 2-CF₃—Ph Cl 4-Ac—Ph Cl 3-Ac—Ph Cl 2-Ac—Ph Cl4-MeO—Ph Cl 3-MeO—Ph Cl 2-MeO—Ph Cl 4-i-PrO—Ph Cl 3-i-PrO—Ph Cl2-i-PrO—Ph Cl 4-I—Ph Cl 3-I—Ph Cl 2-I—Ph Cl 4-Me(C═NH)—Ph Cl3-Me(C═NH)—Ph Cl 2-Me(C═NH)—Ph Cl 4-Me(C═NOMe)—Ph Cl 3-Me(C═NOMe)—Ph Cl2-Me(C═NOMe)—Ph Cl 4-MeNH(C═O)—Ph Cl 3-MeNH(C═O)—Ph Cl 2-MeNH(C═O)—Ph Clpyrid-2-yl Cl pyrid-4-yl Cl 3-CF₃-pyrid-2-yl Cl 4-CF₃-pyrid-2-yl Cl5-CF₃-pyrid-2-yl Cl 6-CF₃-pyrid-2-yl Cl 2-CF₃-pyrid-4-yl Cl3-CF₃-pyrid-4-yl Cl 3-Me-pyrid-2-yl Cl 4-Me-pyrid-2-yl Cl5-Me-pyrid-2-yl Cl 6-Me-pyrid-2-yl Cl 4-Cl-benzyl Cl 3-Cl-benzyl Cl2-Cl-benzyl Cl 4-Br-benzyl Cl 3-Br-benzyl Cl 2-Br-benzyl Cl 4-Et-benzylCl 3-Et-benzyl Cl 2-Et-benzyl Cl 4-CN-benzyl Cl 3-CN-benzyl Cl2-CN-benzyl Cl 4-CF₃-benzyl Cl 3-CF₃-benzyl Cl 2-CF₃-benzyl Cl4-CHF₂-benzyl Cl 3-CHF₂-benzyl Cl 2-CHF₂-benzyl Cl 4-Ac-benzyl Cl3-Ac-benzyl Cl 2-Ac-benzyl Cl 4-MeO-benzyl Cl 3-MeO-benzyl Cl2-MeO-benzyl Cl 4-i-PrO-benzyl Cl 3-i-PrO-benzyl Cl 2-i-PrO-benzyl Clbenzyl Cl methyl Cl n-propyl Cl i-propyl Cl c-propyl Cl n-pentyl Clc-pentyl Cl n-heptyl Me 4-Cl—Ph Me 3-Cl—Ph Me 2-Cl—Ph Me 4-Br—Ph Me3-Br—Ph Me 2-Br—Ph Me 4-Et—Ph Me 3-Et—Ph Me 2-Et—Ph Me 4-CN—Ph Me3-CN—Ph Me 2-CN—Ph Me 4-CF₃—Ph Me 3-CF₃—Ph Me 2-CF₃—Ph Me 4-Ac—Ph Me3-Ac—Ph Me 2-Ac—Ph Me 4-MeO—Ph Me 3-MeO—Ph Me 2-MeO—Ph Me 4-i-PrO—Ph Me3-i-PrO—Ph Me 2-i-PrO—Ph Me 4-Cl-benzyl Me 3-Cl-benzyl Me 2-Cl-benzyl Me4-Br-benzyl Me 3-Br-benzyl Me 2-Br-benzyl Me 4-Et-benzyl Me 3-Et-benzylMe 2-Et-benzyl Me 4-CN-benzyl Me 3-CN-benzyl Me 2-CN-benzyl Me4-CF₃-benzyl Me 3-CF₃-benzyl Me 2-CF₃-benzyl Me 4-CHF₂-benzyl Me3-CHF₂-benzyl Me 2-CHF₂-benzyl Me 4-Ac-benzyl Me 3-Ac-benzyl Me2-Ac-benzyl Me 4-MeO-benzyl Me 3-MeO-benzyl Me 2-MeO-benzyl Me4-i-PrO-benzyl Me 3-i-PrO-benzyl Me 2-i-PrO-benzyl Cl 4-F—Ph Cl 3-F—PhCl 2-F—Ph Cl 4-Me—Ph Cl 3-Me—Ph Cl 2-Me—Ph Cl 4-i-Pr—Ph Cl 3-i-Pr—Ph Cl2-i-Pr—Ph Cl 4-c-Pr—Ph Cl 3-c-Pr—Ph Cl 2-c-Pr—Ph Cl 4-CF₃O—Ph Cl3-CF₃O—Ph Cl 2-CF₃O—Ph Cl 2-(CF₃C═O)—Ph Cl 3-(CF₃C═O)—Ph Cl4-(CF₃C═O)—Ph Cl 4-EtO—Ph Cl 3-EtO—Ph Cl 2-EtO—Ph Cl 4-NO₂—Ph Cl3-NO₂—Ph Cl 2-NO₂—Ph Cl 4-(CO₂Me)—Ph Cl 3-(CO₂Me)—Ph Cl 2-(CO₂Me)—Ph Cl4-Me(C═NMe)—Ph Cl 3-Me(C═NMe)—Ph Cl 2-Me(C═NMe)—Ph Cl 4-Me(C═NOEt)—Ph Cl3-Me(C═NOEt)—Ph Cl 2-Me(C═NOEt)—Ph Cl 4-SiMe₃—Ph Cl 3-SiMe₃—Ph Cl2-SiMe₃—Ph Cl pyrid-3-yl Cl 2,4,6-triazin-1-yl Cl 2-CF₃-pyrid-3-yl Cl4-CF₃-pyrid-3-yl Cl 5-CF₃-pyrid-3-yl Cl 6-CF₃-pyrid-3-yl Cl2-Me-pyrid-4-yl Cl 3-Me-pyrid-4-yl Cl 2-Me-pyrid-3-yl Cl 4-Me-pyrid-3-ylCl 5-Me-pyrid-3-yl Cl 6-Me-pyrid-3-yl Cl 4-F-benzyl Cl 3-F-benzyl Cl2-F-benzyl Cl 4-Me-benzyl Cl 3-Me-benzyl Cl 2-Me-benzyl Cl 4-i-Pr-benzylCl 3-i-Pr-benzyl Cl 2-i-Pr-benzyl Cl 4-c-Pr-benzyl Cl 3-c-Pr-benzyl Cl2-c-Pr-benzyl Cl 4-CF₃O-benzyl Cl 3-CF₃O-benzyl Cl 2-CF₃O-benzyl Cl4-CHF₂O-benzyl Cl 3-CHF₂O-benzyl Cl 2-CHF₂O-benzyl Cl 2-(CF₃C═O)-benzylCl 3-(CF₃C═O)-benzyl Cl 5-(CF₃C═O)-benzyl Cl 4-EtO-benzyl Cl3-EtO-benzyl Cl 2-EtO-benzyl Cl 4-NO₂-benzyl Cl 3-NO₂-benzyl Cl2-NO₂-benzyl Cl phenethyl Cl ethyl Cl n-butyl Cl i-butyl Cl c-butyl Cls-butyl Cl n-hexyl Cl c-hexyl Me 4-F—Ph Me 3-F—Ph Me 2-F—Ph Me 4-Me—PhMe 3-Me—Ph Me 2-Me—Ph Me 4-i-Pr—Ph Me 3-i-Pr—Ph Me 2-i-Pr—Ph Me4-c-Pr—Ph Me 3-c-Pr—Ph Me 2-c-Pr—Ph Me 4-CF₃O—Ph Me 3-CF₃O—Ph Me2-CF₃O—Ph Me 2-(CF₃C═O)—Ph Me 3-(CF₃C═O)—Ph Me 4-(CF₃C═O)—Ph Me 4-EtO—PhMe 3-EtO—Ph Me 2-EtO—Ph Me 4-NO₂—Ph Me 3-NO₂—Ph Me 2-NO₂—Ph Me4-F-benzyl Me 3-F-benzyl Me 2-F-benzyl Me 4-Me-benzyl Me 3-Me-benzyl Me2-Me-benzyl Me 4-i-Pr-benzyl Me 3-i-Pr-benzyl Me 2-i-Pr-benzyl Me4-c-Pr-benzyl Me 3-c-Pr-benzyl Me 2-c-Pr-benzyl Me 4-CF₃O-benzyl Me3-CF₃O-benzyl Me 2-CF₃O-benzyl Me 4-CHF₂O-benzyl Me 3-CHF₂O-benzyl Me2-CHF₂O-benzyl Me 2-(CF₃C═O)-benzyl Me 3-(CF₃C═O)-benzyl Me5-(CF₃C═O)-benzyl Me 4-EtO-benzyl Me 3-EtO-benzyl Me 2-EtO-benzyl Me4-NO₂-benzyl Me 3-NO₂-benzyl Me 2-NO₂-benzylFormulation/Utility

A compound of this invention will generally be used as a fungicidalactive ingredient in a composition, i.e. formulation, with at least oneadditional component selected from the group consisting of surfactants,solid diluents and liquid diluents, which serves as a carrier. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature.

Useful formulations include both liquid and solid compositions. Liquidcompositions include solutions (including emulsifiable concentrates),suspensions, emulsions (including microemulsions and/or suspoemulsions)and the like, which optionally can be thickened into gels. The generaltypes of aqueous liquid compositions are soluble concentrate, suspensionconcentrate, capsule suspension, concentrated emulsion, microemulsionand suspo-emulsion. The general types of nonaqueous liquid compositionsare emulsifiable concentrate, microemulsifiable concentrate, dispersibleconcentrate and oil dispersion.

The general types of solid compositions are dusts, powders, granules,pellets, prills, pastilles, tablets, filled films (including seedcoatings) and the like, which can be water-dispersible (“wettable”) orwater-soluble. Films and coatings formed from film-forming solutions orflowable suspensions are particularly useful for seed treatment. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. An emulsifiablegranule combines the advantages of both an emulsifiable concentrateformulation and a dry granular formulation. High-strength compositionsare primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable mediumbefore spraying. Such liquid and solid formulations are formulated to bereadily diluted in the spray medium, usually water. Spray volumes canrange from about from about one to several thousand liters per hectare,but more typically are in the range from about ten to several hundredliters per hectare. Sprayable formulations can be tank mixed with wateror another suitable medium for foliar treatment by aerial or groundapplication, or for application to the growing medium of the plant.Liquid and dry formulations can be metered directly into drip irrigationsystems or metered into the furrow during planting. Liquid and solidformulations can be applied onto seeds of crops and other desirablevegetation as seed treatments before planting to protect developingroots and other subterranean plant parts and/or foliage through systemicuptake.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersibleand Water- 0.001-90 0-99.999 0-15 soluble Granules, Tablets and PowdersOil Dispersions, Suspensions,    1-50 40-99    0-50 Emulsions, Solutions(including Emulsifiable Concentrates) Dusts    1-25 70-99    0-5 Granules and Pellets 0.001-99 5-99.999 0-15 High Strength Compositions  90-99 0-10    0-2 

Solid diluents include, for example, clays such as bentonite,montmorillonite, attapulgite and kaolin, gypsum, cellulose, titaniumdioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose),silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodiumcarbonate and bicarbonate, and sodium sulfate. Typical solid diluentsare described in Watkins et al., Handbook of Insecticide Dust Diluentsand Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.

Liquid diluents include, for example, water, N,N-dimethylalkanamides(e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide,N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol,triethylene glycol, propylene glycol, dipropylene glycol, polypropyleneglycol, propylene carbonate, butylene carbonate, paraffins (e.g., whitemineral oils, normal paraffins, isoparaffins), alkylbenzenes,alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, triacetin,aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes,alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone,isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamylacetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate,tridecyl acetate and isobornyl acetate, other esters such as alkylatedlactate esters, dibasic esters and γ-butyrolactone, and alcohols, whichcan be linear, branched, saturated or unsaturated, such as methanol,ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol,n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol,isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleylalcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol andbenzyl alcohol. Liquid diluents also include glycerol esters ofsaturated and unsaturated fatty acids (typically C₆-C₂₂), such as plantseed and fruit oils (e.g, oils of olive, castor, linseed, sesame, corn(maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean,rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beeftallow, pork tallow, lard, cod liver oil, fish oil), and mixturesthereof. Liquid diluents also include alkylated fatty acids (e.g.,methylated, ethylated, butylated) wherein the fatty acids may beobtained by hydrolysis of glycerol esters from plant and animal sources,and can be purified by distillation. Typical liquid diluents aredescribed in Marsden, Solvents Guide, 2nd Ed., Interscience, New York,1950.

The solid and liquid compositions of the present invention often includeone or more surfactants. When added to a liquid, surfactants (also knownas “surface-active agents”) generally modify, most often reduce, thesurface tension of the liquid. Depending on the nature of thehydrophilic and lipophilic groups in a surfactant molecule, surfactantscan be useful as wetting agents, dispersants, emulsifiers or defoamingagents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionicsurfactants useful for the present compositions include, but are notlimited to: alcohol alkoxylates such as alcohol alkoxylates based onnatural and synthetic alcohols (which may be branched or linear) andprepared from the alcohols and ethylene oxide, propylene oxide, butyleneoxide or mixtures thereof; amine ethoxylates, alkanolamides andethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylatedsoybean, castor and rapeseed oils; alkylphenol alkoxylates such asoctylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenolethoxylates and dodecyl phenol ethoxylates (prepared from the phenolsand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); block polymers prepared from ethylene oxide or propylene oxideand reverse block polymers where the terminal blocks are prepared frompropylene oxide; ethoxylated fatty acids; ethoxylated fatty esters andoils; ethoxylated methyl esters; ethoxylated tristyrylphenol (includingthose prepared from ethylene oxide, propylene oxide, butylene oxide ormixtures thereof); fatty acid esters, glycerol esters, lanolin-basedderivatives, polyethoxylate esters such as polyethoxylated sorbitanfatty acid esters, polyethoxylated sorbitol fatty acid esters andpolyethoxylated glycerol fatty acid esters; other sorbitan derivativessuch as sorbitan esters; polymeric surfactants such as randomcopolymers, block copolymers, alkyd peg (polyethylene glycol) resins,graft or comb polymers and star polymers; polyethylene glycols (pegs);polyethylene glycol fatty acid esters; silicone-based surfactants; andsugar-derivatives such as sucrose esters, alkyl polyglycosides and alkylpolysaccharides.

Useful anionic surfactants include, but are not limited to: alkylarylsulfonic acids and their salts; carboxylated alcohol or alkylphenolethoxylates; diphenyl sulfonate derivatives; lignin and ligninderivatives such as lignosulfonates; maleic or succinic acids or theiranhydrides; olefin sulfonates; phosphate esters such as phosphate estersof alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates andphosphate esters of styryl phenol ethoxylates; protein-basedsurfactants; sarcosine derivatives; styryl phenol ether sulfate;sulfates and sulfonates of oils and fatty acids; sulfates and sulfonatesof ethoxylated alkylphenols; sulfates of alcohols; sulfates ofethoxylated alcohols; sulfonates of amines and amides such asN,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, anddodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes;sulfonates of naphthalene and alkyl naphthalene; sulfonates offractionated petroleum; sulfosuccinamates; and sulfosuccinates and theirderivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to: amides andethoxylated amides; amines such as N-alkyl propanediamines,tripropylenetriamines and dipropylenetetramines, and ethoxylated amines,ethoxylated diamines and propoxylated amines (prepared from the aminesand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); amine salts such as amine acetates and diamine salts;quaternary ammonium salts such as quaternary salts, ethoxylatedquaternary salts and diquaternary salts; and amine oxides such asalkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic andanionic surfactants or mixtures of nonionic and cationic surfactants.Nonionic, anionic and cationic surfactants and their recommended usesare disclosed in a variety of published references includingMcCutcheon's Emulsifiers and Detergents, annual American andInternational Editions published by McCutcheon's Division, TheManufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopediaof Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; andA. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition,John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliariesand additives, known to those skilled in the art as formulation aids(some of which may be considered to also function as solid diluents,liquid diluents or surfactants). Such formulation auxiliaries andadditives may control: pH (buffers), foaming during processing(antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon's Volume 2: Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typicallyincorporated into the present compositions by dissolving the activeingredient in a solvent or by grinding in a liquid or dry diluent.Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. If the solvent of a liquid compositionintended for use as an emulsifiable concentrate is water-immiscible, anemulsifier is typically added to emulsify the active-containing solventupon dilution with water. Active ingredient slurries, with particlediameters of up to 2,000 μm can be wet milled using media mills toobtain particles with average diameters below 3 μm. Aqueous slurries canbe made into finished suspension concentrates (see, for example, U.S.Pat. No. 3,060,084) or further processed by spray drying to formwater-dispersible granules. Dry formulations usually require dry millingprocesses, which produce average particle diameters in the 2 to 10 μmrange. Dusts and powders can be prepared by blending and usuallygrinding (such as with a hammer mill or fluid-energy mill). Granules andpellets can be prepared by spraying the active material upon preformedgranular carriers or by agglomeration techniques. See Browning,“Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry'sChemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963,pages 8-57 and following, and WO 91/13546. Pellets can be prepared asdescribed in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in U.S. Pat. No.4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can beprepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S.Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture”in Pesticide Chemistry and Bioscience, The Food-Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989; and Developmentsin formulation technology, PJB Publications, Richmond, UK, 2000.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Tables A-B. Without further elaboration, it isbelieved that one skilled in the art using the preceding description canutilize the present invention to its fullest extent. The followingExamples are, therefore, to be constructed as merely illustrative, andnot limiting of the disclosure in any way whatsoever. Percentages are byweight except where otherwise indicated.

Example A High Strength Concentrate

Compound 1 98.5% silica aerogel  0.5% synthetic amorphous fine silica 1.0%

Example B Wettable Powder

Compound 2 65.0% dodecylphenol polyethylene glycol ether  2.0% sodiumligninsulfonate  4.0% sodium silicoaluminate  6.0% montmorillonite(calcined) 23.0%

Example C Granule

Compound 3 10.0% attapulgite granules (low volatile matter, 0.71/0.30mm; 90.0% U.S.S. No. 25-50 sieves)

Example D Extruded Pellet

Compound 4 25.0% anhydrous sodium sulfate 10.0% crude calciumligninsulfonate  5.0% sodium alkylnaphthalenesulfonate  1.0%calcium/magnesium bentonite 59.0%

Example E Emulsifiable Concentrate

Compound 8 10.0% polyoxyethylene sorbitol hexoleate 20.0% C₆-C₁₀ fattyacid methyl ester 70.0%

Example F Microemulsion

Compound 10  5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0%alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water 20.0%

Example G Seed Treatment

Compound 14 20.00% polyvinylpyrrolidone-vinyl acetate copolymer  5.00%montan acid wax  5.00% calcium ligninsulfonate  1.00%polyoxyethylene/polyoxypropylene block copolymers  1.00% stearyl alcohol(POE 20)  2.00% polyorganosilane  0.20% colorant red dye  0.05% water65.75%

The compounds of this invention are useful as plant disease controlagents. The present invention therefore further comprises a method forcontrolling plant diseases caused by fungal plant pathogens comprisingapplying to the plant or portion thereof to be protected, or to theplant seed to be protected, an effective amount of a compound of theinvention or a fungicidal composition containing said compound. Thecompounds and/or compositions of this invention provide control ofdiseases caused by a broad spectrum of fungal plant pathogens in theBasidiomycete, Ascomycete, Oomycete and Deuteromycete classes. They areeffective in controlling a broad spectrum of plant diseases,particularly foliar pathogens of ornamental, turf, vegetable, field,cereal, and fruit crops. These pathogens include: Oomycetes, includingPhytophthora diseases such as Phytophthora infestans, Phytophthoramegasperma, Phytophthora parasitica, Phytophthora cinnamomi andPhytophthora capsici, Pythium diseases such as Pythium aphanidermatum,and diseases in the Peronosporaceae family such as Plasmopara viticola,Peronospora spp. (including Peronospora tabacina and Peronosporaparasitica), Pseudoperonospora spp. (including Pseudoperonosporacubensis) and Bremia lactucae; Ascomycetes, including Alternariadiseases such as Alternaria solani and Alternaria brassicae, Guignardiadiseases such as Guignardia bidwell, Venturia diseases such as Venturiainaequalis, Septoria diseases such as Septoria nodorum and Septoriatritici, powdery mildew diseases such as Erysiphe spp. (includingErysiphe graminis and Erysiphe polygoni), Uncinula necatur, Sphaerothecafuligena and Podosphaera leucotricha, Pseudocercosporellaherpotrichoides, Botrytis diseases such as Botrytis cinerea, Moniliniafructicola, Sclerotinia diseases such as Sclerotinia sclerotiorum,Magnaporthe grisea, Phomopsis viticola, Helminthosporium diseases suchas Helminthosporium tritici repentis, Pyrenophora teres, anthracnosediseases such as Glomerella or Colletotrichum spp. (such asColletotrichum graminicola and Colletotrichum orbiculare), andGaeumannomyces graminis; Basidiomycetes, including rust diseases causedby Puccinia spp. (such as Puccinia recondita, Puccinia striiformis,Puccinia hordei, Puccinia graminis and Puccinia arachidis), Hemileiavastatrix and Phakopsora pachyrhizi; other pathogens includingRhizoctonia spp. (such as Rhizoctonia solani); Fusarium diseases such asFusarium roseum, Fusarium graminearum and Fusarium oxysporum;Verticillium dahliae; Sclerotium rolfsii; Rynchosporium secalis;Cercosporidium personatum, Cercospora arachidicola and Cercosporabeticola; and other genera and species closely related to thesepathogens. In addition to their fungicidal activity, the compositions orcombinations also have activity against bacteria such as Erwiniaamylovora, Xanthomonas campestris, Pseudomonas syringae, and otherrelated species.

Plant disease control is ordinarily accomplished by applying aneffective amount of a compound of this invention either pre- orpost-infection, to the portion of the plant to be protected such as theroots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media(soil or sand) in which the plants to be protected are growing. Thecompounds can also be applied to seeds to protect the seeds andseedlings developing from the seeds. The compounds can also be appliedthrough irrigation water to treat plants.

Rates of application for these compounds can be influenced by manyfactors of the environment and should be determined under actual useconditions. Foliage can normally be protected when treated at a rate offrom less than about 1 g/ha to about 5,000 g/ha of active ingredient.Seed and seedlings can normally be protected when seed is treated at arate of from about 0.1 to about 10 g per kilogram of seed.

Compounds of this invention can also be mixed with one or more otherinsecticides, fungicides, nematocides, bactericides, acaricides, growthregulators, chemosterilants, semiochemicals, repellents, attractants,pheromones, feeding stimulants or other biologically active compounds toform a multi-component pesticide giving an even broader spectrum ofagricultural protection. Examples of such agricultural protectants withwhich compounds of this invention can be formulated are: insecticidessuch as abamectin, acephate, acetamiprid, amidoflumet (S-1955),avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate,buprofezin, carbofuran, cartap, chlorantraniliprole (DPX-E2Y45),chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl,chromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin,cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin,diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin,dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, enestroburin(SYP-Z071), esfenvalerate, ethiprole, fenothiocarb, fenoxycarb,fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide,flucythrinate, tau-fluvalinate, flufenerim (UR-50701), flufenoxuron,fonophos, halofenozide, hexaflumuron, hydramethylnon, imidacloprid,indoxacarb, isofenphos, lufenuron, malathion, metaflumizone,metaldehyde, methamidophos, methidathion, methomyl, methoprene,methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram,nithiazine, novaluron, noviflumuron (XDE-007), oxamyl, parathion,parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon,pirimicarb, profenofos, profluthrin, pymetrozine, pyrafluprole,pyrethrin, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen,rotenone, rynaxypyr, ryanodine, spinetoram, spinosad, spirodiclofen,spiromesifen (BSN 2060), spirotetramat, sulprofos, tebufenozide,teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid,thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate,trichlorfon and triflumuron; fungicides such as acibenzolar-S-methyl,aldimorph, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl,benalaxyl-M, benodanil, benomyl, benthiavalicarb,benthiavalicarb-isopropyl, bethoxazin, binapacryl, biphenyl, bitertanol,bixafen, blasticidin-S, Bordeaux mixture (tribasic copper sulfate),boscalid, bromuconazole, bupirimate, captafol, captan, carbendazim,carboxin, carpropamid, chloroneb, chlorothalonil, chlozolinate,clotrimazole, copper oxychloride, copper salts such as copper sulfateand copper hydroxide, cyazofamid, cyflufenamid, cymoxanil,cyproconazole, cyprodinil, dichlofluanid, diclocymet, diclomezine,dicloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol,dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinocap,dithianon, dodemorph, dodine, edifenphos, enestroburin, epoxiconazole,ethaboxam, ethirimol, etridiazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin chloride, fentinhydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph,fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminum, fuberidazole, furalaxyl, furametpyr, guazatine,hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadinealbesilate, iminoctadine triacetate, iodocarb, ipconazole, iprobenfos,iprodione, iprovalicarb, isoprothiolane, isotianil, kasugamycin,kresoxim-methyl, mancozeb, mandipropamid, maneb, mepanipyrim, mepronil,meptyldinocap, metalaxyl, metalaxyl-M, metconazole, methasulfocarb,metiram, metominostrobin, metrafenone, myclobutanil, naftifine,neo-asozin (ferric methanearsonate), nuarimol, octhilinone, ofurace,orysastrobin, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxin,oxytetracycline, pefurazoate, penconazole, pencycuron, penthiopyrad,phosphorous acid and salts, phthalide, picobenzamid, picoxystrobin,piperalin, polyoxin, probenazole, prochloraz, procymidone, propamocarb,propamocarb-hydrochloride, propiconazole, propineb, proquinazid,prothiocarb, prothioconazole, pryazophos, pyraclostrobin, pyribencarb,pyributicarb, pyrifenox, pyrimethanil, pyrroInitrin, pyroquilon,quinomethionate, quinoxyfen, quintozene, silthiofam, simeconazole,spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tecnazene,terbinafine, tetraconazole, thiabendazole, thifluzamide, thiophanate,thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolyfluanid,triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph,trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole,validamycin, valiphenal, vinclozolin, zineb, ziram, zoxamide,N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazol-4-carboxamide,N-[2-(1S,2R)-[1,1′-bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-1-methyl-11H-pyrazole-4-carboxamide,α-[methoxyimino]-N-methyl-2-[[[1-[3-(trifluoromethyl)-phenyl]-ethoxy]imino]methyl]benzeneacetamide,2-[[[3-(2,6-dichlorophenyl)-1-methyl-2-propen-1-ylidene]amino]oxy]methyl]-α-(methoxyimino)-N-methylbenzeneacetamide,N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanamide,N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)amino]butanamide,2-[[2-fluoro-5-(trifluoromethyl)phenyl]thio]-2-[3-(2-methoxyphenyl)-2-thiazolidinylidene]acetonitrile,2-butoxy-6-iodo-3-propyl-4H-1-benzopyran-4-one,3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine,4-fluorophenylN-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]-methyl]prpyl]carbamate,5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine,N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide,N-[[(cyclopropylmethoxy)amino][6-(difluoromethoxy)-2,3difluorophenyl]methylene]benzeneacetamide,N′-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide,and1-[(2-propenylthio)carbonyl]-2-(1-methylethyl)-4-(2-methylphenyl)-5-amino-1H-pyazol-3-one:nematocides such as aldicarb, imicyafos, oxamyl and fenamiphos;bactericides such as streptomycin; acaricides such as amitraz,chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor,etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate,hexythiazox, propargite, pyridaben and tebufenpyrad; and biologicalagents including entomopathogenic bacteria, such as Bacillusthuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki,and the encapsulated delta-endotoxins of Bacillus thuringiensis (e.g.,Cellcap, MPV, MPVII); entomopathogenic fungi, such as green muscardinefungus; and entomopathogenic virus including baculovirus,nucleopolyhedro virus (NPV) such as HzNPV, AfNPV; and granulosis virus(GV) such as CpGV.

Compounds of this invention and compositions thereof can be applied toplants genetically transformed to express proteins toxic to invertebratepests (such as Bacillus thuringiensis delta-endotoxins). The effect ofthe exogenously applied fungicidal compounds of this invention may besynergistic with the expressed toxin proteins.

General references for agricultural protectants (i.e., insecticides,fungicides, nematocides, acaricides, herbicides and biological agents)include The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed.,British Crop Protection Council, Farnham, Surrey, U.K., 2003 and TheBioPesticide Manual, 2nd Edition, L. G. Copping, Ed., British CropProtection Council, Farnham, Surrey, U.K., 2001.

For embodiments where one or more of these various mixing partners areused, the weight ratio of these various mixing partners (in total) tothe compound of Formula 1 is typically between about 1:100 and about3000:1. Of note are weight ratios between about 1:30 and about 300:1(for example ratios between about 1:1 and about 30:1). It will beevident that including these additional components may expand thespectrum of diseases controlled beyond the spectrum controlled by thecompound of Formula 1 alone.

In one mixture embodiment, granules of a solid composition comprising acompound of Formula 1 is mixed with granules of a solid compositioncomprising another agricultural protectant. These granule mixtures canbe in accordance with the general granule mixture disclosure of PCTPatent Publication WO 94/24861 or more preferably the homogenous granulemixture teaching of U.S. Pat. No. 6,022,552.

Of note are combinations (e.g., in the form of compositions) of (a) acompound of Formula 1 with (b) at least one other fungicide. Ofparticular note are such combinations where the other fungicide hasdifferent site of action from the compound of Formula 1. In certaininstances, combinations with other fungicides having a similar spectrumof control but a different site of action will be particularlyadvantageous for resistance management. Of particular note arecompositions which in addition to a compound of Formula 1 include atleast one compound selected from the group consisting of

(b1) methyl benzimidazole carbamate (MBC) fungicides;

(b2) dicarboximide fungicides;

(b3) demethylation inhibitor (DMI) fungicides;

(b4) phenylamide fungicides;

(b5) amine/morpholine fungicides;

(b6) phospholipid biosynthesis inhibitor fungicides;

(b7) carboxamide fungicides;

(b8) hydroxy(2-amino-)pyrimidine fungicides;

(b9) anilinopyrimidine fungicides;

(b10) N-phenyl carbamate fungicides;

(b11) quinone outside inhibitor (QoI) fungicides;

(b12) phenylpyrrole fungicides;

(b13) quinoline fungicides;

(b14) lipid peroxidation inhibitor fungicides;

(b15) melanin biosynthesis inhibitors-reductase (MBI-R) fungicides;

(b16) melanin biosynthesis inhibitors-dehydratase (MBI-D) fungicides;

(b17) hydroxyanilide fungicides;

(b18) squalene-epoxidase inhibitor fungicides;

(b19) polyoxin fungicides;

(b20) phenylurea fungicides;

(b21) quinone inside inhibitor (QiI) fungicides;

(b22) benzamide fungicides;

(b23) enopyranuronic acid antibiotic fungicides;

(b24) hexopyranosyl antibiotic fungicides;

(b25) glucopyranosyl antibiotic: protein synthesis fungicides;

(b26) glucopyranosyl antibiotic: trehalase and inositol biosynthesisfungicides;

(b27) cyanoacetamideoxime fungicides;

(b28) carbamate fungicides;

(b29) oxidative phosphorylation uncoupling fungicides;

(b30) organo tin fungicides;

(b31) carboxylic acid fungicides;

(b32) heteroaromatic fungicides;

(b33) phosphonate fungicides;

(b34) phthalamic acid fungicides;

(b35) benzotriazine fungicides;

(b36) benzene-sulfonamide fungicides;

(b37) pyridazinone fungicides;

(b38) thiophene-carboxamide fungicides;

(b39) pyrimidinamide fungicides;

(b40) carboxylic acid amide (CAA) fungicides;

(b41) tetracycline antibiotic fungicides;

(b42) thiocarbamate fungicides;

(b43) benzamide fungicides;

(b44) host plant defense induction fungicides;

(b45) multi-site contact activity fungicides;

(b46) fungicides other than fungicides of component (a) and components(b1) through (b45); and

salts of compounds of (b1) through (b46).

“Methyl benzimidazole carbamate (MBC) fungicides (b1)” (FungicideResistance Action Committee (FRAC) code 1) inhibit mitosis by binding toβ-tubulin during microtubule assembly. Inhibition of microtubuleassembly can disrupt cell division, transport within the cell and cellstructure. Methyl benzimidazole carbamate fungicides includebenzimidazole and thiophanate fungicides. The benzimidazoles includebenomyl, carbendazim, fuberidazole and thiabendazole. The thiophanatesinclude thiophanate and thiophanate-methyl.

“Dicarboximide fungicides (b2)” (Fungicide Resistance Action Committee(FRAC) code 2) are proposed to inhibit a lipid peroxidation in fungithrough interference with NADH cytochrome c reductase. Examples includechlozolinate, iprodione, procymidone and vinclozolin.

“Demethylation inhibitor (DMI) fungicides (b3)” (Fungicide ResistanceAction Committee (FRAC) code 3) inhibit C14-demethylase which plays arole in sterol production. Sterols, such as ergosterol, are needed formembrane structure and function, making them essential for thedevelopment of functional cell walls. Therefore, exposure to thesefungicides result in abnormal growth and eventually death of sensitivefungi. DMI fungicides are divided between several chemical classes:azoles (including triazoles and imidazoles), pyrimidines, piperazinesand pyridines. The triazoles include azaconazole, bitertanol,bromuconazole, cyproconazole, difenoconazole, diniconazole (includingdiniconazole-M), epoxiconazole, fenbuconazole, fluquinconazole,flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole,metconazole, myclobutanil, penconazole, propiconazole, prothioconazole,simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol,triticonazole and uniconazole. The imidazoles include clotrimazole,imazalil, oxpoconazole, prochloraz, pefurazoate and triflumizole. Thepyrimidines include fenarimol and nuarimol. The piperazines includetriforine. The pyridines include pyrifenox. Biochemical investigationshave shown that all of the above mentioned fungicides are DMI fungicidesas described by K. H. Kuck et al. in Modern SelectiveFungicides—Properties, Applications and Mechanisms of Action, H. Lyr(Ed.), Gustav Fischer Verlag: New York, 1995, 205-258.

“Phenylamide fungicides (b4)” (Fungicide Resistance Action Committee(FRAC) code 4) are specific inhibitors of RNA polymerase in Oomycetefungi. Sensitive fungi exposed to these fungicides show a reducedcapacity to incorporate uridine into rRNA. Growth and development insensitive fungi is prevented by exposure to this class of fungicide.Phenylamide fungicides include acylalanine, oxazolidinone andbutyrolactone fungicides. The acylalanines include benalaxyl,benalaxyl-M, furalaxyl, metalaxyl and metalaxyl-M/mefenoxam. Theoxazolidinones include oxadixyl. The butyrolactones include ofurace.

“Amine/morpholine fungicides (b5)” (Fungicide Resistance ActionCommittee (FRAC) code 5) inhibit two target sites within the sterolbiosynthetic pathway, Δ⁸-Δ⁷ isomerase and Δ¹⁴ reductase. Sterols, suchas ergosterol, are needed for membrane structure and function, makingthem essential for the development of functional cell walls. Therefore,exposure to these fungicides results in abnormal growth and eventuallydeath of sensitive fungi. Amine/morpholine fungicides (also known asnon-DMI sterol biosynthesis inhibitors) include morpholine, piperidineand spiroketal-amine fungicides. The morpholines include aldimorph,dodemorph, fenpropimorph, tridemorph and trimorphamide. The piperidinesinclude fenpropidin and piperalin. The spiroketal-amines includespiroxamine.

“Phospholipid biosynthesis inhibitor fungicides (b6)” (FungicideResistance Action Committee (FRAC) code 6) inhibit growth of fungi byaffecting phospholipid biosynthesis. Phospholipid biosynthesisfungicides include phosphorothiolate and dithiolane fungicides. Thephosphorothiolates include edifenphos, iprobenfos and pyrazophos. Thedithiolanes include isoprothiolane.

“Carboxamide fungicides (b7)” (Fungicide Resistance Action Committee(FRAC) code 7) inhibit Complex II (succinate dehydrogenase) fungalrespiration by disrupting a key enzyme in the Krebs Cycle (TCA cycle)named succinate dehydrogenase. Inhibiting respiration prevents thefungus from making ATP, and thus inhibits growth and reproduction.Carboxamide fungicides include benzamide, furan carboxamide, oxathiincarboxamide, thiazole carboxamide, pyrazole carboxamide and pyridinecarboxamide. The Benzamides include benodanil, flutolanil and mepronil.The furan carboxamides include fenfuram. The oxathiin carboxamideinclude carboxin and oxycarboxin. The thiazole carboxamides includethifluzamide. The pyrazole carboxamides include furametpyr,penthiopyrad, bixafen,N-[2-(1S,2R)-[1,1′-bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamideandN-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide.The pyridine carboxamide include boscalid.

“Hydroxy(2-amino-)pyrimidine fungicides (b8)” (Fungicide ResistanceAction Committee (FRAC) code 8) inhibit nucleic acid synthesis byinterfering with adenosine deaminase. Examples include bupirimate,dimethirimol and ethirimol.

“Anilinopyrimidine fungicides (b9)” (Fungicide Resistance ActionCommittee (FRAC) code 9) are proposed to inhibit biosynthesis of theamino acid methionine and to disrupt the secretion of hydrolytic enzymesthat lyse plant cells during infection. Examples include cyprodinil,mepanipyrim and pyrimethanil.

“N-Phenyl carbamate fungicides (b10)” (Fungicide Resistance ActionCommittee (FRAC) code 10) inhibit mitosis by binding to β-tubulin anddisrupting microtubule assembly. Inhibition of microtubule assembly candisrupt cell division, transport within the cell and cell structure.Examples include diethofencarb.

“Quinone outside inhibitor (QoI) fungicides (b 11)” (FungicideResistance Action Committee (FRAC) code 11) inhibit Complex IIImitochondrial respiration in fungi by affecting ubiquinol oxidase.Oxidation of ubiquinol is blocked at the “quinone outside” (Q_(O)) siteof the cytochrome bc₁ complex, which is located in the innermitochondrial membrane of fungi. Inhibiting mitochondrial respirationprevents normal fungal growth and development. Quinone outside inhibitorfungicides (also known as strobilurin fungicides) includemethoxyacrylate, methoxycarbamate, oximinoacetate, oximinoacetamide,oxazolidinedione, dihydrodioxazine, imidazolinone and benzylcarbamatefungicides. The methoxyacrylates include azoxystrobin, enestroburin(SYP-Z071) and picoxystrobin. The methoxycarbamates includepyraclostrobin. The oximinoacetates include kresoxim-methyl andtrifloxystrobin. The oximinoacetamides include dimoxystrobin,metominostrobin, orysastrobin,α-[methoxyimino]-N-methyl-2-[[[1-[3-(trifluoromethyl)phenyl]-ethoxy]imino]methyl]benzeneacetamideand2-[[[3-(2,6-dichlorophenyl)-1-methyl-2-propen-1-ylidene]amino]oxy]methyl]-α-(methoxyimino)-N-methylbenzeneacetamide.The oxazolidinediones include famoxadone. The dihydrodioxazines includefluoxastrobin. The imidazolinones include fenamidone. Thebenzylcarbamates include pyribencarb.

“Phenylpyrrole fungicides (b12)” (Fungicide Resistance Action Committee(FRAC) code 12) inhibit a MAP protein kinase associated with osmoticsignal transduction in fungi. Fenpiclonil and fludioxonil are examplesof this fungicide class.

“Quinoline fungicides (b13)” (Fungicide Resistance Action Committee(FRAC) code 13) are proposed to inhibit signal transduction by affectingG-proteins in early cell signaling. They have been shown to interferewith germination and/or appressorium formation in fungi that causepowder mildew diseases. Quinoxyfen is an example of this class offungicide.

“Lipid peroxidation inhibitor fungicides (b14)” (Fungicide ResistanceAction Committee (FRAC) code 14) are proposed to inhibit lipidperoxidation which affects membrane synthesis in fungi. Members of thisclass, such as etridiazole, may also affect other biological processessuch as respiration and melanin biosynthesis. Lipid peroxidationfungicides include aromatic carbon and 1,2,4-thiadiazole fungicides. Thearomatic carbons include biphenyl, chloroneb, dicloran, quintozene,tecnazene and tolclofos-methyl. The 1,2,4-thiadiazoles includeetridiazole.

“Melanin biosynthesis inhibitors-reductase (MBI-R) fungicides (b15)”(Fungicide Resistance Action Committee (FRAC) code 16.1) inhibit thenaphthal reduction step in melanin biosynthesis. Melanin is required forhost plant infection by some fungi. Melanin biosynthesisinhibitors-reductase fungicides include isobenzofuranone,pyrroloquinolinone and triazolobenzothiazole fungicides. Theisobenzofuranones include fthalide. The pyrroloquinolinones includepyroquilon. The triazolobenzothiazoles include tricyclazole.

“Melanin biosynthesis inhibitors-dehydratase (MBI-D) fungicides (b16)”(Fungicide Resistance Action Committee (FRAC) code 16.2) inhibitscytalone dehydratase in melanin biosynthesis. Melanin in required forhost plant infection by some fungi. Melanin biosynthesisinhibitors-dehydratase fungicides include cyclopropanecarboxamide,carboxamide and propionamide fungicides. The cyclopropanecarboxamidesinclude carpropamid. The carboxamides include diclocymet. Thepropionamides include fenoxanil.

“Hydroxyanilide fungicides (b17)” (Fungicide Resistance Action Committee(FRAC) code 17) inhibit C4-demethylase which plays a role in sterolproduction. Examples include fenhexamid.

“Squalene-epoxidase inhibitor fungicides (b18)” (Fungicide ResistanceAction Committee (FRAC) code 18) inhibit squalene-epoxidase inergosterol biosynthesis pathway. Sterols such as ergosterol are neededfor membrane structure and function making them essential for thedevelopment of functional cell walls. Therefore exposure to thesefungicides result in abnormal growth and eventually death of sensitivefungi. Squalene-epoxidase inhibitor fungicides include thiocarbamate andallylamine fungicides. The thiocarbamates include pyributicarb. Theallylamines include naftifine and terbinafine.

“Polyoxin fungicides (b19)” (Fungicide Resistance Action Committee(FRAC) code 19) inhibit chitin synthase. Examples include polyoxin.

“Phenylurea fungicides (b20)” (Fungicide Resistance Action Committee(FRAC) code 20) are proposed to affect cell division. Examples includepencycuron.

“Quinone inside inhibitor (QiI) fungicides (b21)” (Fungicide ResistanceAction Committee (FRAC) code 21) inhibit Complex III mitochondrialrespiration in fungi by affecting ubiquinol reductase. Reduction ofubiquinol is blocked at the “quinone inside” (Qi) site of the cytochromebc₁ complex, which is located in the inner mitochondrial membrane offungi. Inhibiting mitochondrial respiration prevents normal fungalgrowth and development. Quinone inside inhibitor fungicides includecyanoimidazole and sulfamoyltriazole fungicides. The cyanoimidazolesinclude cyazofamid. The sulfamoyltriazoles include amisulbrom.

“Benzamide fungicides (b22)” (Fungicide Resistance Action Committee(FRAC) code 22) inhibit mitosis by binding to j3-tubulin and disruptingmicrotubule assembly. Inhibition of microtubule assembly can disruptcell division, transport within the cell and cell structure. Examplesinclude zoxamide.

“Enopyranuronic acid antibiotic fungicides (b23)” (Fungicide ResistanceAction Committee (FRAC) code 23) inhibit growth of fungi by affectingprotein biosynthesis. Examples include blasticidin-S.

“Hexopyranosyl antibiotic fungicides (b24)” (Fungicide Resistance ActionCommittee (FRAC) code 24) inhibit growth of fungi by affecting proteinbiosynthesis. Examples include kasugamycin.

“Glucopyranosyl antibiotic: protein synthesis fungicides (b25)”(Fungicide Resistance Action Committee (FRAC) code 25) inhibit growth offungi by affecting protein biosynthesis. Examples include streptomycin.

“Glucopyranosyl antibiotic: trehalase and inositol biosynthesisfungicides (b26)” (Fungicide Resistance Action Committee (FRAC) code 26)inhibit trehalase in inositol biosynthesis pathway. Examples includevalidamycin.

“Cyanoacetamideoxime fungicides (b27) (Fungicide Resistance ActionCommittee (FRAC) code 27) include cymoxanil.

“Carbamate fungicides (b28)” (Fungicide Resistance Action Committee(FRAC) code 28) are considered multi-site inhibitors of fungal growth.They are proposed to interfere with the synthesis of fatty acids in cellmembranes, which then disrupts cell membrane permeability. Propamacarb,propamacarb-hydrochloride, iodocarb, and prothiocarb are examples ofthis fungicide class.

“Oxidative phosphorylation uncoupling fungicides (b29)” (FungicideResistance Action Committee (FRAC) code 29) inhibit fungal respirationby uncoupling oxidative phosphorylation. Inhibiting respiration preventsnormal fungal growth and development. This class includes2,6-dinitroanilines such as fluazinam, pyrimidonehydrazones such asferimzone and dinitrophenyl crotonates such as dinocap, meptyldinocapand binapacryl.

“Organo tin fungicides (b30)” (Fungicide Resistance Action Committee(FRAC) code 30) inhibit adenosine triphosphate (ATP) synthase inoxidative phosphorylation pathway. Examples include fentin acetate,fentin chloride and fentin hydroxide.

“Carboxylic acid fungicides (b31)” (Fungicide Resistance ActionCommittee (FRAC) code 31) inhibit growth of fungi by affectingdeoxyribonucleic acid (DNA) topoisomerase type II (gyrase). Examplesinclude oxolinic acid.

“Heteroaromatic fungicides (b32)” (Fungicide Resistance Action Committee(FRAC) code 32) are proposed to affect DNA/ribonucleic acid (RNA)synthesis. Heteroaromatic fungicides include isoxazole and isothiazolonefungicides. The isoxazoles include hymexazole and the isothiazolonesinclude octhilinone.

“Phosphonate fungicides (b33)” (Fungicide Resistance Action Committee(FRAC) code 33) include phosphorous acid and its various salts,including fosetyl-aluminum.

“Phthalamic acid fungicides (b34)” (Fungicide Resistance ActionCommittee (FRAC) code 34) include teclofthalam.

“Benzotriazine fungicides (b35)” (Fungicide Resistance Action Committee(FRAC) code 35) include triazoxide.

“Benzene-sulfonamide fungicides (b36)” (Fungicide Resistance ActionCommittee (FRAC) code 36) include flusulfamide.

“Pyridazinone fungicides (b37)” (Fungicide Resistance Action Committee(FRAC) code 37) include diclomezine.

“Thiophene-carboxamide fungicides (b38)” (Fungicide Resistance ActionCommittee (FRAC) code 38) are proposed to affect ATP production.Examples include silthiofam.

“Pyrimidinamide fungicides (b39)” (Fungicide Resistance Action Committee(FRAC) code 39) inhibit growth of fungi by affecting phospholipidbiosynthesis and include diflumetorim.

“Carboxylic acid amide (CAA) fungicides (b40)” (Fungicide ResistanceAction Committee (FRAC) code 40) are proposed to inhibit phospholipidbiosynthesis and cell wall deposition. Inhibition of these processesprevents growth and leads to death of the target fungus. Carboxylic acidamide fungicides include cinnamic acid amide, valinamide carbamate andmandelic acid amide fungicides. The cinnamic acid amides includedimethomorph and flumorph. The valinamide carbamates includebenthiavalicarb, benthiavalicarb-isopropyl, iprovalicarb and valiphenal.The mandelic acid amides include mandipropamid,N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]-ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanamideandN-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)amino]butanamide.

“Tetracycline antibiotic fungicides (b41)” (Fungicide Resistance ActionCommittee (FRAC) code 41) inhibit growth of fungi by affecting complex 1nicotinamide adenine dinucleotide (NADH) oxidoreductase. Examplesinclude oxytetracycline.

“Thiocarbamate fungicides (b42)” (Fungicide Resistance Action Committee(FRAC) code 42) include methasulfocarb.

“Benzamide fungicides (b43)” (Fungicide Resistance Action Committee(FRAC) code 43) inhibit growth of fungi by delocalization ofspectrin-like proteins. Examples include acylpicolide fungicides such asfluopicolide and fluopyram.

“Host plant defense induction fungicides (b44)” (Fungicide ResistanceAction Committee (FRAC) code P) induce host plant defense mechanisms.Host plant defense induction fungicides include benzo-thiadiazole,benzisothiazole and thiadiazole-carboxamide fungicides. Thebenzo-thiadiazoles include acibenzolar-5-methyl. The benzisothiazolesinclude probenazole. The thiadiazole-carboxamides include tiadinil andisotianil.

“Multi-site contact fungicides (b45)” inhibit fungal growth throughmultiple sites of action and have contact/preventive activity. Thisclass of fungicides includes: “copper fungicides (b45.1) (FungicideResistance Action Committee (FRAC) code M1)”, “sulfur fungicides (b45.2)(Fungicide Resistance Action Committee (FRAC) code M2)”,“dithiocarbamate fungicides (b45.3) (Fungicide Resistance ActionCommittee (FRAC) code M3)”, “phthalimide fungicides (b45.4) (FungicideResistance Action Committee (FRAC) code M4)”, “chloronitrile fungicides(b45.5) (Fungicide Resistance Action Committee (FRAC) code M5)”,“sulfamide fungicides (b45.6) (Fungicide Resistance Action Committee(FRAC) code M6)”, “guanidine fungicides (b45.7) (Fungicide ResistanceAction Committee (FRAC) code M7)” “triazines fungicides (b45.8)(Fungicide Resistance Action Committee (FRAC) code M8)” and “quinonefungicides (b45.9) (Fungicide Resistance Action Committee (FRAC) codeM9)”. “Copper fungicides” are inorganic compounds containing copper,typically in the copper(II) oxidation state; examples include copperoxychloride, copper sulfate and copper hydroxide, including compositionssuch as Bordeaux mixture (tribasic copper sulfate). “Sulfur fungicides”are inorganic chemicals containing rings or chains of sulfur atoms;examples include elemental sulfur. “Dithiocarbamate fungicides” containa dithiocarbamate molecular moiety; examples include mancozeb, metiram,propineb, ferbam, maneb, thiram, zineb and ziram. “Phthalimidefungicides” contain a phthalimide molecular moiety; examples includefolpet, captan and captafol. “Chloronitrile fungicides” contain anaromatic ring substituted with chloro and cyano; examples includechlorothalonil. “Sulfamide fungicides” include dichlofluanid andtolyfluanid. “Guanidine fungicides” include dodine, guazatine,iminoctadine albesilate and iminoctadine triacetate. “Triazinesfungicides” include anilazine. “Quinone fungicides” include dithianon.

“Fungicides other than fungicides of component (a) and components (b11)through (b45); (b46)” include certain fungicides considered to have anunknown mode of action. These include: “thiazole carboxamide fungicide(b46.1) (Fungicide Resistance Action Committee (FRAC) code US)”,“phenyl-acetamide fungicide (b46.2) (Fungicide Resistance ActionCommittee (FRAC) code U6)”, “quinazolinone fungicide (b46.3) (FungicideResistance Action Committee (FRAC) code U7)” and “benzophenone fungicide(b46.4) (Fungicide Resistance Action Committee (FRAC) code U8)”. Thethiazole carboxamides include ethaboxam. The phenyl-acetamides includecyflufenamid andN-[[(cyclopropylmethoxy)amino][6-(difluoromethoxy)-2,3-difluorophenyl]-methylene]benzeneacetamide.The quinazolinones include proquinazid,6-bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone,6,8-diiodo-3-propyl-2-propyloxy-4-(3H)-quinazolinone,6-chloro-2-propoxy-3-propylthieno[2,3-d]pyrimidin-4(3H)-one,2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one,6-bromo-2-propoxy-3-propylthieno[2,3-d]pyrimidin-4(3H)-one,7-bromo-2-propoxy-3-propylthieno[3,2-d]pyrimidin-4(3H)-one,6-bromo-2-propoxy-3-propylpyrido[2,3-d]pyrimidin-4(3H)-one,6,7-dibromo-2-propoxy-3-propylthieno[3,2-d]pyrimidin-4(3H)-one,3-(cyclopropylmethyl)-6-iodo-2-(propylthio)pyrido[2,3-d]pyrimidin-4(3H)-one,2-butoxy-6-iodo-3-propyl-4H-1-benzopyran-4-one,2-ethoxy-6-iodo-3-propyl-4H-1-benzopyran-4-one,6-iodo-2-propoxy-3-propyl-4H-1-benzopyran-4-one,2-(2-butynyloxy)-6-iodo-3-propyl-4H-1-benzopyran-4-one,6-iodo-2-(1-methylbutoxy)-3-propyl-4H-1-benzopyran-4-one,2-(3-butenyloxy)-6-iodo-3-propyl-4H-1-benzopyran-4-one,3-butyl-6-iodo-2-(1-methylethoxy)-4H-1-benzopyran-4-one, and6-iodo-3-propyl-2H-1,3-benzoxazine-2,4(3H)-dione 2-(O-methyloxime). Thebenzophenones include metrafenone. The (b46) group also includesbethoxazin, neo-asozin (ferric methanearsonate), pyrroInitrin,quinomethionate,5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine(BAS600), 3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine(SYP-Z048), 4-fluorophenylN-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]methyl]propyl]carbamate(XR-539),N-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide,2-[[2-fluoro-5-(trifluoromethyl)phenyl]thio]-2-[3-(2-methoxyphenyl)-2-thiazolidinylidene]acetonitrile(OK-5203) andN-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide (TF-991).

Embodiments of the present invention include:

Embodiment D1

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b1)methyl benzimidazole carbamate fungicides such as benomyl, carbendazimand thiophanate-methyl.

Embodiment D2

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b2)dicarboximide fungicides such as procymidone, iprodione and vinclozolin.

Embodiment D3

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b3)demethylation inhibitor fungicides such as epoxiconazole,fluquinconazole, triadimenol, simeconazole, ipconazole, triforine,cyproconazole, difenconazole, flusilazole, flutriafol, metconazole,myclobutanil, prochloraz, propiconazole, prothioconazole, tebuconazoleand tetraconazole.

Embodiment D4

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b4)phenylamide fungicides such as metalaxyl, metalaxyl-M, benalaxyl,benalaxyl-M, furalaxyl, ofurace and oxadixyl.

Embodiment D5

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b5)amine/morpholine fungicides such as aldimorph, dodemorph, fenpropimorph,tridemorph, trimorphamide. fenpropidin, piperalin and spiroxamine.

Embodiment D6

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b6)phospholipid biosynthesis inhibitor fungicides such as edifenphos andisoprothiolane.

Embodiment D7

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b7)carboxamide fungicides such as boscalid, penthiopyrad, bixafen, carboxinand oxycarboxin.

Embodiment D8

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b8)hydroxy(2-amino-)pyrimidine fungicides such as ethirimol.

Embodiment D9

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b9)anilinopyrimidine fungicides such as cyprodinil.

Embodiment D10

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 29 and A through D)wherein component (b) includes at least one compound selected from (b10)N-phenyl carbamate fungicides such as diethofencarb.

Embodiment D11

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b11)quinone outside inhibitor fungicides such as azoxystrobin,pyraclostrobin, kresoxim-methyl, trifloxystrobin, picoxystrobin,pyribencarb, famoxadone, fenamidone, enestrobin, dimoxystrobin,metominostrobin, orysastrobin and fluoxastrobin.

Embodiment D12

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 31 and A through C5)wherein component (b) includes at least one compound selected from (b12)phenylpyrrole fungicides compound such as fenpiclonil and fludioxonil.

Embodiment D13

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b13)quinoline fungicides such as quinoxyfen.

Embodiment D14

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b14)lipid peroxidation inhibitor fungicides such as chloroneb.

Embodiment D15

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b15)melanin biosynthesis inhibitors-reductase fungicides such as pyroquilonand tricyclazole.

Embodiment D16

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b16)melanin biosynthesis inhibitors-dehydratase fungicides such ascarpropamid.

Embodiment D17

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b17)hydroxyanilide fungicides such as fenhexamid.

Embodiment D18

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b18)squalene-epoxidase inhibitor fungicides such as pyributicarb.

Embodiment D19

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b19)polyoxin fungicides such as polyoxin.

Embodiment D20

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b20)phenylurea fungicides such as pencycuron.

Embodiment D21

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b21)quinone inside inhibitor fungicides such as cyazofamid and amisulbrom.

Embodiment D22

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b22)benzamide fungicides such as zoxamide.

Embodiment D23

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b23)enopyranuronic acid antibiotic fungicides such as blasticidin-S.

Embodiment D24

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b24)hexopyranosyl antibiotic fungicides such as kasugamycin.

Embodiment D25

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b25)glucopyranosyl antibiotic: protein synthesis fungicides such asstreptomycin.

Embodiment D26

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b26)glucopyranosyl antibiotic: trehalase and inositol biosynthesisfungicides such as validamycin.

Embodiment D27

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b27)cyanoacetylamideoxime fungicides such as cymoxanil.

Embodiment D28

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b28)carbamate fungicides such as propamacarb, propamacarb-hydrochloride,prothiocarb and iodocarb.

Embodiment D29

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b29)oxidative phosphorylation uncoupling fungicides such as fluazinam,binapacryl, ferimzone, meptyldinocap and dinocap.

Embodiment D30

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b30)organo tin fungicides such as fentin acetate.

Embodiment D31

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b31)carboxylic acid fungicides such as oxolinic acid.

Embodiment D32

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b32)heteroaromatic fungicides such as hymexazole.

Embodiment D33

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b33)phosphonate fungicides such as phosphorous acid and its various salts,including fosetyl-aluminum.

Embodiment D34

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b34)phthalamic acid fungicides such as teclofthalam.

Embodiment D35

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b35)benzotriazine fungicides such as triazoxide.

Embodiment D36

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b36)benzene-sulfonamide fungicides such as flusulfamide.

Embodiment D37

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b37)pyridazinone fungicides such as diclomezine.

Embodiment D38

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b38)thiophene-carboxamide fungicides such as silthiofam.

Embodiment D39

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b39)pyrimidinamide fungicides such as diflumetorim.

Embodiment D40

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b40)carboxylic acid amide fungicides such as dimethomorph, benthiavalicarb,benthiavalicarb-isopropyl, iprovalicarb, valiphenal, mandipropamid andflumorph.

Embodiment D41

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b41)tetracycline antibiotic fungicides such as oxytetracycline.

Embodiment D42

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b42)thiocarbamate fungicides such as methasulfocarb.

Embodiment D43

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b43)benzamide fungicides such as fluopicolide and fluopyram.

Embodiment D44

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b44)host plant defense induction fungicides such as acibenzolar-5-methyl.

Embodiment D45

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b45)multi-site contact fungicides such as copper oxychloride, coppersulfate, copper hydroxide, Bordeaux composition (tribasic coppersulfide), elemental sulfur, mancozeb, metiram, propineb, ferbam, maneb,thiram, zineb, ziram, folpet, captan, captafol and chlorothalonil.

Embodiment D46

The composition described in the Summary of the Invention (including butnot limited to composition of Embodiments 1 through 32 and A through C5)wherein component (b) includes at least one compound selected from (b46)fungicides other than fungicides of component (a) and components (b1)through (b45) such as ethaboxam, cyflufenamid, proquinazid, metrafenone,5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine,2-butoxy-6-iodo-3-propyl-4H-1-benzopyran-4-one,3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine,4-fluorophenylN-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]methyl]propyl]carbamate,N-[[(cyclopropylmethoxy)amino][6-(difluormethoxy)-2,3-difluorophenyl]methylene]benzeneacetamide,N′-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide,2-[[2-fluoro-5-(trifluoromethyl)phenyl]thio]-2-[3-(2-methoxyphenyl)-2-thiazolidinylidene]acetonitrileand N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide.

The following TESTS demonstrate the control efficacy of compounds ofthis invention on specific pathogens. The pathogen control protectionafforded by the compounds is not limited, however, to these species. SeeIndex Tables A-J for compound descriptions. See Index Table K for ¹H NMRdata. The following abbreviations are used in the Index Tables whichfollow: i means iso, c means cyclo, n means normal, t means tertiary, Acis acetyl, Me is methyl, Et is ethyl, Ph is phenyl, Bn is benzyl, OMe ismethoxy, OEt is ethoxy, SMe is methylthio and CN is cyano. Substituentson benzyl are attached to the phenyl ring of the benzyl, and locantnumbers for the substituents are relative to the phenyl position bondedto the methylene component of benzyl. The abbreviation “Ex.” stands for“Example” and is followed by a number indicating in which example thecompound is prepared. The abbreviation MP stands for “melting point”.

INDEX TABLE A

Cmpd. R¹ R⁴ Q V¹ R^(10a) R^(10b) R^(10c) MP  1 (Ex. 1) Cl OMe CH₂ CH₂CH₂Me Me Me **  2 (Ex. 2) Cl OMe CH₂ CH₂CH₂CH₂ Me Me Me **  3 Cl OMe CH₂CH₂C(═CH₂)CH₂ Me Me Me *  4 Cl OMe CH₂ CH₂ Me Me CH═CH₂ *  5 Cl OMe CH₂CH₂ Me Me 4-Cl—Ph *  6 Cl OMe CH₂ CH₂ Me Me Me *  7 Cl OMe CH₂ CH₂ Me MeEt * 15 Cl OMe CH₂ CH₂ Me Me Ph * 16 Cl OMe CH₂ CH₂ Me Me 4-F—Ph * 17 ClOMe CH₂ CH₂ Me Me Bn * *See Index Table K for ¹H NMR data. **Seesynthesis example for ¹H NMR data.

INDEX TABLE B

Cmpd. R¹ R⁴ Q R¹⁴ MP  8 (Ex. 3) Cl OMe NH 3-OCF₃ **  9 Cl OMe NH4-SiMe₃ * 10 Cl OEt NH 4-OCF₃ * 11 Cl OMe NH 4-OCF₃ * 12 Cl OMe NH4-CN * 13 Cl OMe NH 4-SCH₃ * 14 Cl OMe CH₂ 4-SiMe₃ * 18 Cl OMe O3-OCF₃ * 19 Cl OMe O 3-Cl * *See Index Table K for ¹H NMR data. **Seesynthesis example for ¹H NMR data.

INDEX TABLE C

Cmpd. R¹ R⁴ Q R^(14a) R^(14b) A MP  20 Cl OMe CH₂(6-methyl-pyrid-2-yl)-CH₂— H CH *  21 Cl OMe CH₂ H H CH *  22 Cl OMe CH₂3-methyl-1-butyl H CH *  23 Cl OMe CH₂ 1-(3-trimethylsilyl-propyl)- HCH *  24 Cl OMe CH₂ 1-pent-4-ynyl H CH *  25 Cl OMe CH₂(2-chloro-thiazol-5-yl)-CH₂— H CH *  26 Cl OMe CH₂ —CH₂CN H CH *  27 ClOMe CH₂ (ethyl-dimethylsilyl)-CH₂— H CH *  28 Cl OMe CH₂ methyl H CH * 29 Cl OMe CH₂ 1-(1-trimethylsilyl-ethyl)- H CH *  30 Cl OMe CH₂1-(4-methyl-pent-3-enyl)- H CH *  31 Cl OMe CH₂ —CH₂CH₂CN H CH *  32 ClOMe CH₂ —CH₂CH₂CH₂CN H CH *  34 Cl OMe CH₂ Ph H CH *  35 Cl OMe CH₂Me₂NSO₂— H CH *  36 Cl OMe CH₂ 1-[4,4-bis-(4-fluorophenyl)- H CH *butyl]  37 Cl OMe CH₂ 2-Cl-benzyl H CH *  38 Cl OMe CH₂ 3-CF₃-benzyl HCH *  39 Cl OMe CH₂ 1-pent-4-ynyl Me CH *  40 Cl OMe CH₂1-(3-trimethylsilyl-propyl)- Me CH *  41 Cl OMe CH₂ 1-(4-methyl-pentyl)-H CH *  42 Cl OMe CH₂ 1-(3-phenyl-propyl)- H CH *  43 Cl OMe CH₂1-(3-fluoro-propyl)- H CH *  45 Cl OMe CH₂ 1-(3-trimethylsilyl-propyl)-CF₃ CH *  46 Cl OMe CH₂ butyl H CH *  47 Cl OMe CH₂1-(3-trimethylsilyl-propyl)- H CCl *  48 Cl OMe CH₂ 5-methyl-pyrid-2-ylH CH *  49 Cl OMe CH₂ 6-methyl-pyrid-2-yl H CH *  50 Cl OMe CH₂ 3-CF₃—PhH CH *  51 Cl OMe CH₂ 2-CF₃—Ph H CH *  52 Cl OMe CH₂ 2-Cl—Ph H CH *  53Cl OMe CH₂ 2-Cl-5-CF₃-benzyl H CH *  54 Cl OMe CH₂ 2-Ac—Ph H CH *  55 ClOMe CH₂ 4-(2-CN—Ph)-benzyl H CH *  56 Cl OMe CH₂ 3-[1-(4-chloro-phenyl)-H CH * propane-1-one]  57 Cl OMe CH₂ benzyl H CH *  58 Cl OMe CH₂phenethyl H CH *  59 Cl OMe CH₂ 1-(2-phenoxy-ethyl) H CH *  60 Cl OMeCH₂ 3-Cl-benzyl H CH *  61 Cl OMe CH₂ 1-(2-phenoxy-propyl) H CH *  62 ClOMe CH₂ 2-CF₃-benzyl H CH *  63 Cl OMe CH₂ 4-CF₃-benzyl H CH *  64 ClOMe NH 3-CF₃—Ph H CH *  65 Cl OMe CH₂ 3-OCF₃-benzyl H CH *  66 Cl OMeCH₂ 4-OCF₃-benzyl H CH *  67 Cl OMe CH₂ 4-Cl-benzyl H CH 134-139  68 ClOMe CH₂ 3-OCF₃—Ph H CH 136-138  69 Cl OMe CH₂ 6-CF₃-pyrid-2-yl H CH171-173  70 Cl OMe CH₂ 2-Me-benzyl H CH *  71 Cl OMe CH₂ 3-Me-benzyl HCH *  72 Cl OMe CH₂ 4-Me-benzyl H CH 126-129  73 Cl OMe CH₂ 3-NO₂-benzylH CH *  74 Cl OMe CH₂ 4-Cl—Ph H CH 151-153  75 Cl OMe CH₂ 3-CN-benzyl HCH *  76 Cl OMe CH₂ 2-OCF₃-benzyl H CH *  77 Cl OMe CH₂ 4-OCF₃—Ph H CH149-151  78 Cl OMe CH₂ 3,5-di-CF₃—Ph H CH 164-166  79 Cl OMe CH₂4-CF₃—Ph H CH 180  80 Cl OMe CH₂ 3-Cl—Ph H CH 127-129  81 Cl OMe CH₂3-Me—Ph H CH 115-118  82 Cl OMe CH₂ 4-Ph—Ph H CH 172-174  86 Cl OMe CH₂4-CF₃-pyrid-2-yl H CH 169-171  87 Cl OMe CH₂ 4-CF₃-pyrimid-2-yl H CH155-158  88 Cl OMe CH₂ 4-Cl-3-CF₃—Ph H CH 165-180  89 Cl OMe CH₂3-CF₃—Ph H N 160-163  90 Cl OMe CH₂ 3,5-di-MeO-triazin-1-yl H CH *  91Cl OMe CH₂ 3-BnS-1,2,4-thiadiazol-5-yl H CH *  92 Cl OMe CH₂3-MeO-1,2,4-thiadiazol-5-yl H CH *  93 Cl OMe CH₂3-EtS-1,2,4-thiadiazol-5-yl H CH *  94 Cl OMe CH₂ 3-(4-CF₃—Ph)-1,2,4- HCH * thiadiazol-5-yl  95 Cl OMe CH₂ 3-c-Pr-1,2,4-thiadiazol-5-yl H CH * 96 Cl OMe CH₂ 3-t-Bu-1,2,4-thiadiazol-5-yl H CH *  97 Cl OMe CH₂4-Br—Ph H N 160-163  98 Cl OMe CH₂ Me n-pentyl CH *  99 Cl OMe CH₂ H4-t-bu—Ph CH * 100 Cl OMe CH₂ H CF₃ CH * 101 Cl OMe CH₂1-(3,3-dimethylbutyl) CF₃ CH * 102 Cl OMe CH₂ n-butyl CF₃ CH * 103 ClOMe CH₂ n-propyl CF₃ CH * 104 Cl OMe CH₂ 3-(2-propyl)-1,2,4- H CH *thiadiazol-5-yl 105 Cl OMe CH₂ 3-Me-1,2,4-thiadiazol-5-yl H CH * 106 ClOMe CH₂ 4-MeO—Ph H CH * 107 Cl OMe CH₂ 3-MeO—Ph H CH * 108 Cl OMe CH₂4-(MeO₂C)—Ph H CH * 109 Cl OMe CH₂ 4-Me—Ph H CH * 110 Cl OMe CH₂4-(i-propyl)—Ph H CH * 111 Cl OMe CH₂ 4-Br—Ph H CH * 112 Cl OMe CH₂3-Br—Ph H CH * 113 Cl OMe CH₂ 3-CN—Ph H CH * 114 Cl OMe CH₂ 4-CN—Ph HCH * 115 Cl OMe CH₂ 3-F—Ph H CH * 116 Cl OMe CH₂ 4-F—Ph H CH * 117 ClOMe CH₂ 3,4-di-Cl—Ph H CH * 118 Cl OMe CH₂ 3,4-di-F—Ph H CH * 150 Cl OMeCH₂ 4-Ac—Ph H CH * *See Index Table K for ¹H NMR data.

INDEX TABLE D

Cmpd. R¹ R⁴ Q R^(14a) A MP 119 Cl OMe CH₂ 3-CF₃—Ph CH 125-130 120 Cl OMeCH₂ 3-CF₃—Ph N 155-157 121 Cl OMe CH₂ 3-Br—Ph CH 137-140 122 Cl OMe CH₂4-Cl—Ph CH 152-155 123 (Ex. 15) Cl OMe CH₂ 3-Cl—Ph CH 127-130 124 Cl OMeCH₂ 4-Br—Ph CH 168-170

INDEX TABLE E

Cmpd. R¹ R⁴ Q R¹⁴ MP 126 Cl OMe CH₂ 3-trimethylsilyl-1-propyl * 127 ClOMe CH₂ H * 128 Cl OMe CH₂ benzyl * 129 Cl OMe CH₂ 2-Cl-benzyl *

INDEX TABLE F

Cmpd. R¹ R⁴ Q R^(14a) R^(14b) A MP 130 Cl OMe CH₂ Cl H CH * 131 Cl OMeCH₂ 2-Me-thiazol-4-yl H CH * 132 Cl OMe CH₂ 4-Me—Ph H CH * 133 Cl OMeCH₂ 3-Me—Ph H CH * 134 Cl OMe CH₂ Ph H CH * 137 Cl OMe CH₂ c-propyl HCH * 138 Cl OMe CH₂ CF₃ H CH * 139 Cl OMe CH₂ BnO H CH * *See IndexTable K for ¹H NMR data.

INDEX TABLE G

Cmpd. R¹ R⁴ Q R^(14a) R^(14b) A MP 140 Cl OMe CH₂ Ph H CH * 141 Cl OMeCH₂ Me CF₃ CH * 142 Cl OMe CH₂ 1-(3,3- CF₃ CH * dimethyl-butyl) 143 ClOMe CH₂ i-butyl CF₃ CH * 144 Cl OMe CH₂ n-propyl CF₃ CH * *See IndexTable K for ¹H NMR data.

INDEX TABLE H

Cmpd. R¹ R⁴ Q R¹⁴ MP 145 Cl OMe CH₂ H * 148 Cl OMe CH₂ 4-Cl—Ph * 149 ClOMe CH₂ 4-Me-benzyl * *See Index Table K for ¹H NMR data.

INDEX TABLE I

Cmpd. R¹ R⁴ Q R¹⁴ MP 146 Cl OMe CH₂ 4-Me-benzyl * 147 Cl OMe CH₂4-Cl—Ph * *See Index Table K for ¹H NMR data.

INDEX TABLE J

Cmpd. R¹ R⁴ V Q R^(14a) R^(14b) Mp 83 Me OMe — C═O 3-CF₃—Ph H * 84 MeOMe — C═NOMe 3-CF₃—Ph H * 85 Me (NH)Me — C═NOMe 3-CF₃—Ph H * *See IndexTable K for ¹H NMR data. A dash (“—”) indicates a direct bond.

INDEX TABLE K Com- pound No. ¹H NMR Data (CDCl₃ solution unlessindicated otherwise)^(a) 1 δ 7.66 (br s, 1H), 7.51 (m, 1H), 7.34 (d,1H), 5.21 (br s, 1H), 4.46 (d, 2H), 4.28 (m, 2H), 3.69 (s, 3H), 2.20 (s,3H), 1.09 (m, 2H), 0.06 (s, 9H). 2 δ 7.66 (br s, 1H), 7.52 (m, 1H), 7.35(m, 1H), 5.18 (m, 1H), 4.46 (d, 2H), 4.14 (m, 2H), 3.69 (s, 3H), 2.21(s, 3H), 1.71 (m, 2H), 0.54 (m, 2H), 0.01 (m, 9H). 3 δ 7.66 (br s, 1H),7.53 (m, 1H), 7.35 (d, 1H), 5.18 (br s, 1H), 4.92 (d, 1H), 4.74 (s, 1H),4.58 (s, 2H), 4.46 (d, 2H), 3.70 (s, 3H), 2.25 (s, 3H), 1.60 (s, 2H),0.06 (m, 9H). 4 δ 7.65 (m, 1H), 7.50 (m, 1H), 7.34 (d, 1H), 6.20 (m,1H), 6.03 (m, 1H), 5.79 (m, 1H), 5.19 (s, 1H), 4.45 (d, 2H), 4.04 (s,2H), 3.69 (s, 3H), 2.18 (s, 3H), 0.20 (m, 6 H). 5 δ 7.62 (s, 1H), 7.51(m, 2H), 7.44 (m, 1H), 7.33 (m, 3H), 5.18 (s, 1H), 4.44 (d, 2H), 4.17(s, 2H), 3.68 (s, 3H), 2.15 (s, 3H), 0.38 (m, 6 H). 6 δ 7.66 (s, 1H),7.51 (m, 1H), 7.35 (d, 1H), 5.18 (s, 1H), 4.47 (d, 2H), 3.98 (s, 2H),3.70 (s, 3H), 2.19 (s, 3H), 0.13 (m, 9H). 7 δ 7.65 (s, 1H), 7.49 (m,1H), 7.33 (d, 1H), 5.25 (s, 1H), 4.45 (d, 2H), 4.00 (s, 2H), 3.68 (s,3H), 2.17 (s, 3H), 1.00 (m, 3H), 0.62 (m, 2H), 0.09 (m, 6 H) 8 δ 7.45(m, 2H), 7.35 (m, 2H), 7.20 (m, 1H), 7.11 (d, 1H), 7.02 (dd, 1H), 6.55(br, 1H), 6.32 (br s, 1H), 3.78 (s, 3H). 9 δ 7.59 (d, 2H), 7.52 (d, 2H),7.33 (d, 1H), 7.15 (d, 1H), 7.05 (dd, 1H), 6.53 (br s, 1H), 6.29 (br s,1H), 3.78 (s, 3H), 0.30 (s, 9H). 10 δ 7.54 (d, 2H), 7.35 (d, 1H), 7.27(d, 2H), 7.11 (d, 1H), 7.00 (dd, 1H), 6.49 (br s, 1H), 6.31 (br s, 1H),4.22 (q, 2H), 1.28 (m, 3H). 11 δ 7.54 (d, 2H), 7.34 (d, 1H), 7.27 (d,2H), 7.10 (d, 1H), 7.00 (dd, 1H), 6.49 (br s, 1H), 6.31 (br s, 1H), 3.78(s, 3H). 12 δ 7.71 (d, 2H), 7.65 (d, 2H), 7.38 (d, 1H), 7.05 (d, 1H),7.03 (dd, 1H), 6.54 (br s, 1H), 6.33 (br s, 1H), 3.78 (s, 3H). 13 δ 7.46(d, 2H), 7.33 (d, 1H), 7.31 (d, 2H), 7.11 (d, 1H), 7.02 (dd, 1H), 6.51(br, 1H), 6.29 (br, 1H), 3.77 (s, 3H), 2.52 (s, 3H). 14 δ 7.60 (m, 3H),7.54 (d, 2H), 7.43 (m, 2H), 5.18 (br s, 1H), 4.51 (d, 2H), 3.69 (s, 3H),0.30 (s, 9H). 15 δ 7.62 (br s, 1H), 7.59 (br m, 2H), 7.46 (br d, 1H),7.38 (br m, 3H), 7.33 (br d, 1H), 4.45 (br d, 2H), 4.19 (s, 2H), 3.69(s, 3H), 2.17 (s, 3H). 0.4 (s, 6H). 16 δ 7.63 (br s, 1H), 7.56 (m, 2H),7.46 (d, 1H), 7.33 (d, 1H), 7.07 (t, 2H), 4.45 (d, 2H), 4.16 (s, 2H),3.69 (s, 3H), 2.16 (s, 3H), 0.4 (s, 6H). 17 δ 7.66 (br s, 1H), 7.50 (d,1H), 7.35 (d, 1H), 7.21 (t, 2H), 7.08 (t, 1H), 7.04 (d, 2H), 4.46 (m,2H), 3.98 (s, 2H), 3.68 (s, 3H), 2.22 (s, 2H), 2.17 (s, 3H), 0.1 (s,6H). 18 δ 7.85 (s, 1H), 7.52 (d, 1H), 7.45 (m, 3H), 7.38 (s, 1H), 7.23(m, 1H), 7.20 (d, 1H), 3.86 (s, 3H). 19 δ 7.84 (s, 1H), 7.52 (m, 1H),7.51 (d, 1H), 7.41 (m, 2H), 7.37 (d, 1H), 7.34 (m, 1H), 7.19 (m, 1H),3.86 (s, 3H). 20 δ 7.82 (s, 1H), 7.69 (d, 1H), 7.53 (m, 2H), 7.38 (d,1H), 7.07 (d, 1H), 6.81 (d, 1H), 6.59 (d, 1H), 5.46 (s, 2H), 5.17 (br s,1H), 4.50 (d, 2H), 3.69 (s, 3H), 2.57 (s, 3H). 21 δ 7.80 (s, 1H), 7.64(m, 2H), 7.41 (d, 1H), 6.62 (d, 1H), 5.19 (br s, 1H), 4.50 (d, 2H), 3.70(s, 3H). 22 δ 7.80 (s, 1H), 7.66 (d, 1H), 7.39 (d, 1H), 7.37 (d, 1H),6.50 (d, 1H), 5.17 (br s, 1H), 4.49 (d, 2H), 4.15 (m, 2H), 3.69 (s, 3H),1.80 (m, 2H), 1.63 (m, 1H), 0.97 (d, 6 H). 23 δ 7.80 (s, 1H), 7.67 (d,1H), 7.40 (d, 1H), 7.37 (d, 1H), 6.51 (d, 1H), 5.15 (br s, 1H), 4.49 (brs, 2H), 4.11 (m, 2H), 3.69 (s, 3H), 1.88 (m, 2H), 0.50 (m, 2H), 0.00 (s,9H). 24 δ 7.80 (s, 1H), 7.66 (d, 1H), 7.44 (d, 1H), 7.38 (d, 1H), 6.51(d, 1H), 5.15 (br s, 1H), 4.49 (d, 2H), 4.29 (m, 2H), 3.69 (s, 3H), 2.21(m, 2H), 2.15 (m, 1H), 2.12 (m, 2H), 2.03 (m, 1H). 25 δ 7.80 (s, 1H),7.66 (d, 1H), 7.51 (s, 1H), 7.45 (d, 1H), 7.38 (d, 1H), 6.56 (d, 1H),5.44 (s, 2H), 5.27 (br s, 1H), 4.49 (d, 2H), 3.70 (s, 3H). 26 δ 7.81 (s,1H), 7.66 (d, 1H), 7.58 (d, 1H), 7.40 (d, 1H), 6.65 (d, 1H), 5.19 (br s,1H), 5.11 (s, 2H), 4.50 (m, 2H), 3.70 (s, 3H). 27 δ 7.77 (d, 1H), 7.65(d, 1H), 7.35 (d, 1H), 7.27 (d, 1H), 6.49 (d, 1H), 5.14 (br s, 1H), 4.49(d, 2H), 3.77 (s, 2H), 3.70 (s, 3H), 0.96 (m, 3H), 0.63 (m, 2H), 0.11(s, 6 H). 28 δ 7.80 (s, 1H), 7.66 (d, 1H), 7.38 (m, 2H), 6.52 (d, 1H),5.15 (br s, 1H), 4.50 (d, 2H), 3.95 (s, 3H), 3.70 (s, 3H). 29 δ 7.78 (s,1H), 7.66 (d, 1H), 7.35 (d, 1H), 7.32 (d, 1H), 6.49 (d, 1H), 5.14 (br s,1H), 4.49 (d, 2H), 3.86 (m, 1H), 3.70 (s, 3H), 1.56 (d, 3H), 0.09 (s,9H). 30 δ 7.80 (s, 1H), 7.66 (d, 1H), 7.38 (s, 1H), 7.36 (m, 1H), 6.49(d, 1H), 5.16 (br s, 1H), 5.10 (m, 1H), 4.50 (d, 2H), 4.12 (m, 2H), 3.69(s, 3H), 2.57 (m, 2H), 1.99 (m, 1H), 1.69 (s, 3H), 1.53 (s, 3H). 31 δ7.81 (s, 1H), 7.64 (d, 1H), 7.52 (d, 1H), 7.39 (d, 1H), 6.56 (d, 1H),5.19 (br s., 1H), 4.50 (d, 2H), 4.42 (m, 2H), 3.70 (s, 3H), 3.01 (m,2H). 32 δ 7.80 (s, 1H), 7.65 (d, 1H), 7.45 (d, 1H), 7.38 (d, 1H), 6.54(d, 1H), 5.19 (br s, 1H), 4.49 (d, 2H), 4.30 (m, 2H), 3.69 (s, 3H), 2.34(m, 4H). 34 δ 7.95 (d, 1H), 7.92 (s, 1H), 7.76 (m, 3H), 7.47 (m, 2H),7.41 (d, 1H), 7.30 (m, 1H), 6.76 (d, 1H), 5.21 (br s, 1H), 4.52 (d, 2H),3.70 (s, 3H). 35 δ 8.19 (s, 1H), 7.97 (s, 1H), 7.53 (s, 1H), 7.38 (m,2H), 5.27 (br s, 1H), 4.47 (d, 2H), 3.70 (s, 3H), 2.99 (m, 6H). 36 δ7.79 (s, 1H), 7.64 (d, 1H), 7.37 (d, 1H), 7.34 (d, 1H), 7.11 (m, 4 H),6.95 (m, 4 H), 6.51 (d, 1H), 5.17 (br s, 1H), 4.49 (d, 2H), 4.14 (m,2H), 3.88 (m, 1H), 3.67 (s, 3H), 1.99 (m, 2H), 1.86 (m, 2H). 37 δ 7.69(d, 1H), 7.56 (d, 1H), 7.36 (d, 1H), 7.28 (d, 1H), 7.23 (d, 1H), 7.12(m, 2H), 6.88 (d, 1H), 6.47 (d, 1H), 5.56 (br s, 1H), 5.35 (s, 2H), 4.37(d, 2H), 3.57 (s, 3H). 38 δ 7.82 (s, 1H), 7.68 (d, 1H), 7.57 (m, 1H),7.52 (s, 1H), 7.48 (m, 1H), 7.40 (m, 3H), 6.59 (d, 1H), 5.41 (s, 2H),5.17 (br s, 1H), 4.50 (d, 2H), 3.69 (s, 3H). 39 δ 7.76 (s, 1H), 7.62 (d,1H), 7.35 (d, 1H), 6.28 (s, 1H), 5.19 (br s, 1H), 4.48 (d, 2H), 4.17 (m,2H), 3.69 (s, 3H), 2.34 (s, 3H), 2.22 (m, 2H), 2.11 (m, 2H), 2.02 (t,1H). 40 δ 7.77 (s, 1H), 7.62 (d, 1H), 7.36 (d, 1H), 6.29 (s, 1H), 5.14(br s, 1H), 4.49 (d, 2H), 4.03 (m, 2H), 3.70 (s, 3H), 2.31 (s, 3H), 1.84(m, 2H), 0.52 (m, 2H), 0.00 (m, 9H). 41 δ 7.80 (s, 1H), 7.66 (d, 1H),7.38 (m, 2H), 6.51 (d, 1H), 5.15 (br s, 1H), 4.50 (d, 2H), 4.12 (m, 2H),3.69 (s, 3H), 1.91 (m, 2H), 1.58 (m, 1H), 1.22 (m, 2H), 0.89 (d, 6 H).42 δ 7.80 (s, 1H), 7.66 (d, 1H), 7.37 (m, 2H), 7.29 (m, 2H), 7.20 (m,3H), 6.51 (d, 1H), 5.19 (br s, 1H), 4.49 (d, 2H), 4.14 (m, 2H), 3.68 (s,3H), 2.65 (m, 2H), 2.25 (m, 2H). 43 δ 7.80 (s, 1H), 7.65 (d, 1H), 7.43(d, 1H), 7.37 (d, 1H), 6.52 (d, 1H), 5.21 (br s, 1H), 4.50 (m, 3H), 4.39(m, 1H), 4.30 (m, 2H), 3.69 (s, 3H), 2.30 (m, 2H). 45 δ 7.78 (s, 1H),7.64 (d, 1H), 7.39 (d, 1H), 6.84 (s, 1H), 5.22 (br s, 1H), 4.49 (d, 2H),4.19 (m, 2H), 3.69 (s, 3H), 1.91 (m, 2H), 0.52 (m, 2H), 0.00 (s, 9H). 46δ 7.80 (s, 1H), 7.66 (d, 1H), 7.38 (d, 1H), 7.36 (s, 0 H), 6.50 (d, 1H),5.16 (br s, 1H), 4.49 (d, 2H), 4.14 (m, 2H), 3.69 (s, 3H), 1.88 (m, 2H),1.36 (m, 2H), 0.96 (m, 3H). 47 δ 7.92 (s, 1H), 7.77 (d, 1H), 7.43 (m,2H), 5.15 (br s, 1H), 4.51 (d, 2H), 4.06 (m, 2H), 3.69 (s, 3H), 1.86 (m,2H), 0.49 (m, 2H), 0.00 (s, 9H). 48 δ 8.55 (d, 1H), 8.23 (s, 1H), 7.98(d, 1H), 7.94 (s, 1H), 7.78 (d, 1H), 7.64 (d, 1H), 7.42 (d, 1H), 6.75(d, 1H), 5.20 (br s, 1H), 4.53 (d, 2H), 3.71 (s, 3H), 2.37 (s, 3H). 498.62 (d, 1H), 7.94 (s, 1H), 7.87 (d, 1H), 7.79 (d, 1H), 7.71 (m, 1H),7.42 (d, 1H), 7.04 (d, 1H), 6.75 (d, 1H), 5.20 (br s, 1H), 4.53 (d, 2H),3.71 (s, 3H), 2.57 (s, 3H). 50 δ 8.05 (s, 1H), 8.01 (d, 1H), 7.93 (m,2H), 7.79 (d, 1H), 7.58 (m, 2H), 7.43 (d, 1H), 6.80 (d, 1H), 5.22 (br s,1H), 4.53 (d, 2H), 3.71 (s, 3H). 51 δ 7.88 (s, 1H), 7.82 (m, 1H), 7.72(m, 3H), 7.64 (m, 2H), 7.41 (d, 1H), 6.76 (d, 1H), 5.15 (br s, 1H), 4.50(br s, 2H), 3.70 (s, 3H). 52 δ 7.92 (d, 1H), 7.90 (s, 1H), 7.76 (d, 1H),7.68 (d, 1H), 7.54 (d, 1H), 7.41 (m, 2H), 7.36 (m, 1H), 6.77 (d, 1H),5.18 (br s, 1H), 4.51 (d, 2H), 3.70 (s, 3H). 53 δ 7.81 (s, 1H), 7.68 (d,1H), 7.52 (m, 3H), 7.39 (d, 1H), 6.62 (d, 1H), 5.50 (s, 2H), 5.16 (br s,1H), 4.50 (d, 2H), 3.69 (s, 3H). 54 δ 8.31 (s, 1H), 8.04 (m, 2H), 7.93(s, 1H), 7.88 (d, 1H), 7.80 (d, 1H), 7.59 (m, 1H), 7.43 (d, 1H), 6.80(d, 1H), 5.22 (br s, 1H), 4.53 (d, 2H), 3.71 (s, 3H), 2.69 (s, 3H). 55 δ7.83 (s, 1H), 7.74 (d, 1H), 7.69 (d, 1H), 7.62 (m, 1H), 7.54 (d, 2H),7.45 (m, 3H), 7.36 (m, 3H), 6.59 (d, 1H), 5.41 (s, 2H), 5.24 (br s, 1H),4.49 (d, 2H), 3.68 (s, 3H). 56 δ 7.90 (m, 2H), 7.79 (s, 1H), 7.61 (d,1H), 7.52 (d, 1H), 7.43 (d, 2H), 7.36 (d, 1H), 6.47 (d, 1H), 5.16 (br s,1H), 4.61 (m, 2H), 4.48 (d, 2H), 3.69 (s, 3H), 3.61 (m, 2H). 57 δ 7.81(s, 1H), 7.68 (d, 1H), 7.35 (m, 4 H), 7.26 (s, 3H), 6.55 (d, 1H), 5.35(s, 2H), 5.17 (br s, 1H), 4.49 (d, 2H), 3.70 (s, 3H). 58 δ 7.81 (s, 1H),7.68 (d, 1H), 7.38 (d, 1H), 7.27 (m, 3H), 7.16 (d, 1H), 7.11 (d, 2H),6.44 (d, 1H), 5.18 (br s, 1H), 4.51 (d, 2H), 4.36 (m, 2H), 3.70 (s, 3H),3.20 (t, 2H). 59 δ 7.79 (s, 1H), 7.64 (d, 1H), 7.55 (d, 1H), 7.36 (d,1H), 7.26 (m, 2H), 6.95 (m, 1H), 6.87 (d, 2H), 6.51 (d, 1H), 5.22 (br s,1H), 4.52 (m, 2H), 4.48 (d, 2H), 4.35 (m, 2H), 3.68 (s, 3H). 60 δ 7.81(s, 1H), 7.68 (d, 1H), 7.39 (m, 2H), 7.28 (m, 2H), 7.22 (s, 1H), 7.12(m, 1H), 6.58 (d, 1H), 5.32 (s, 2H), 5.18 (br s, 1H), 4.49 (d, 2H), 3.69(s, 3H). 61 δ 7.79 (s, 1H), 7.64 (d, 1H), 7.38 (m, 2H), 7.28 (m, 2H),6.96 (d, 1H), 6.89 (d, 2H), 6.48 (d, 1H), 5.17 (br s, 1H), 4.49 (d, 2H),4.38 (m, 2H), 3.94 (m, 2H), 3.69 (s, 3H), 2.38 (m, 2H). 62 δ 7.83 (s,1H), 7.69 (d, 2H), 7.43 (m, 4 H), 7.02 (d, 1H), 6.61 (d, 1H), 5.58 (s,2H), 5.21 (br s, 1H), 4.49 (d, 2H), 3.69 (s, 3H) 63 δ 7.82 (s, 1H), 7.67(d, 1H), 7.60 (d, 2H), 7.42 (d, 1H), 7.38 (d, 1H), 7.33 (d, 2H), 6.59(d, 1H), 5.41 (s, 2H), 5.19 (br s, 1H), 4.49 (d, 2H), 3.69 (s, 3H). 64 δ8.0 (s, 1H), 7.98 (s, 1H), 7.90 (d, 1H), 7.59 (t, 1H), 7.5 (d, 1H), 7.4(s, 1H), 7.3 (d, 1H), 7.1 (d, 1H), 6.7 (s, 1H), 6.58 (br s, 1H), 5.7(brs, 1H), 3.7(s, 3H), 2.2(s, 3H). 65 δ 7.81 (s, 1H), 7.67 (m, 1H), 7.39(m, 3H), 7.15 (t, 2H), 7.08 (s, 1H), 6.59 (d, 1H), 5.36 (s, 2H), 5.20(br s, 1H), 4.49 (d, 2H), 3.69 (s, 3H). 66 δ 7.81 (s, 1H), 7.67 (d, 1H),7.54 (m, 1H), 7.38 (m, 2H), 7.26 (m, 1H), 7.19 (m, 2H), 6.58 (d, 1H),5.35 (s, 2H), 5.19 (br s, 1H), 4.49 (d, 2H), 3.69 (s, 3H). 70 δ 7.81 (s,1H), 7.68 (d, 1H), 7.37 (d, 1H), 7.22 (m, 4 H), 7.05 (d, 1H), 6.53 (d,1H), 5.34 (s, 2H), 5.21 (br s, 1H), 4.49 (d, 2H), 3.68 (s, 3H), 2.30 (s,3H). 71 δ 7.81 (s, 1H), 7.68 (d, 1H), 7.36 (m, 2H), 7.25 (m, 1H), 7.12(d, 1H), 7.05 (m, 2H), 6.54 (d, 1H), 5.30 (s, 2H), 5.20 (br s, 1H), 4.49(d, 2H), 3.68 (s, 3H), 2.33 (s, 3H). 73 δ 8.17 (m, 1H), 8.12 (s, 1H),7.81 (s, 1H), 7.67 (d, 1H), 7.55 (m, 2H), 7.47 (d, 1H), 7.38 (d, 1H),6.62 (d, 1H), 5.45 (s, 2H), 5.21 (br s, 1H), 4.49 (d, 2H), 3.69 (s, 3H).75 δ 7.81 (s, 1H), 7.67 (d, 1H), 7.60 (m, 1H), 7.49 (s, 1H), 7.45 (m,3H), 7.38 (d, 1H), 6.61 (d, 1H), 5.38 (s, 2H), 5.22 (br s, 1H), 4.49 (d,2H), 3.68 (s, 3H). 76 δ 7.80 (s, 1H), 7.67 (d, 1H), 7.43 (d, 1H), 7.29(m, 4 H), 7.11 (d, 1H), 6.57 (d, 1H), 5.43 (s, 2H), 5.22 (br s, 1H),4.48 (d, 2H), 3.68 (s, 3H). 83 δ 8.2 (s, 1H), 8.0-8.1 (m, 3H), 7.9 (d,1H), 7.5-7.6 (m, 2H), 7.4 (d, 1H), 6.8 (d, 1H), 4.0 (s, 3H), 2.6 (s,3H). 84 δ 8.0 (s, 1H), 7.99 (d, 1H), 7.9 (d, 1H), 7.8 (d, 1H), 7.63 (s,1H), 7.5-7.6 (m, 2H), 7.3 (d, 1H), 6.7 (d, 1H), 4.07 (s, 3H), 3.89 (s,3H), 2.23 (s, 3H). 85 δ 8.0 (s, 1H), 7.99 (d, 1H), 7.9 (d, 1H), 7.8 (d,1H), 7.63 (s, 1H), 7.5-7.6 (m, 2H), 7.3 (d, 1H), 6.7 (d, 1H), ), 3.89(s, 3H), 2.9 (d, 3H), 2.2 (s, 3H). 90 δ 8.63 (d, 1H), 7.96 (s, 1H), 7.86(d, 1H), 7.44 (d, 1H), 6.83 (d, 1H), 5.20 (br s, 1H), 4.52 (d, 2H), 4.16(s, 6 H), 3.70 (s, 3H) 91 δ 8.29 (d, 1H), 7.87 (s, 1H), 7.75 (d, 1H),7.46 (m, 3H), 7.31 (m, 3H), 6.82 (d, 1H), 5.25 (br, 1H), 4.51 (m, 4H),3.71 (s, 3H). 92 δ 8.27 (d, 1H), 7.86 (s, 1H), 7.73 (d, 1H), 7.43 (d,1H), 6.81 (d, 1H), 5.32 (br s, 1H), 4.51 (d, 2H), 4.11 (s, 3H), 3.71 (s,3H). 93 δ 8.28 (d, 1H), 7.86 (s, 1H), 7.73 (d, 1H), 7.44 (d, 1H), 6.81(d, 1H), 5.31 (br s, 1H), 4.51 (d, 2H), 3.71 (s, 3H), 3.26 (m, 2H), 1.47(t, 3H). 94 δ 8.43 (d, 1H), 8.41 (d, 2H), 7.91 (s, 1H), 7.78 (d, 1H),7.76 (d, 2H), 7.46 (d, 1H), 6.88 (d, 1H), 5.27 (br s, 1H), 4.53 (d, 2H),3.72 (s, 3H). 95 δ 8.25 (d, 1H), 7.84 (s, 1H), 7.71 (d, 1H), 7.41 (d,1H), 6.77 (d, 1H), 5.37 (br s, 1H), 4.49 (d, 2H), 3.70 (s, 3H), 2.27 (m,1H), 1.15 (m, 2H), 1.06 (m, 2H). 96 δ 8.32 (d, 1H), 7.85 (s, 1H), 7.73(d, 1H), 7.39 (m, 1H), 6.78 (d, 1H), 5.44 (br s, 1H), 4.49 (d, 2H), 3.70(s, 3H), 1.45 (s, 9H). 98 δ 7.44 (d, 1H), 7.36 (d, 1H), 7.26 (m, 1H),5.25 (br s, 1H), 4.48 (d, 2H), 3.81 (s, 3H), 3.69 (s, 3H), 2.6 (m, 2H),1.67 (m, 2H), 1.37 (m, 4H), 0.92 (m, 3H). 99 δ 7.80 (s, 1H), 7.57 (m,3H), 7.39 (m, 3H), 6.74 (s, 1H), 5.72 (br s, 1H), 5.34 (br s, 1H), 4.41(d, 2H), 3.62 (s, 3H), 1.34 (s, 9H). 100 (DMSO-d₆) δ 7.82 (s, 1H), 7.74(d, 1H), 7.65 (m, 1H), 7.57 (d, 1H), 7.19 (s, 1H), 4.31 (d, 2H), 3.59(s, 3H). 101 δ 7.78 (s, 1H), 7.63 (d, 1H), 7.39 (d, 1H), 6.84 (s, 1H),5.24 (br s, 1H), 4.47 (d, 2H), 4.24 (t, 2H), 3.70 (s, 3H), 1.83 (m, 2H),1.01 (s, 9H). 102 δ 7.79 (s, 1H), 7.63 (d, 1H), 7.39 (d, 1H), 6.85 (s,1H), 5.23 (br s, 1H), 4.49 (d, 2H), 4.23 (t, 2H), 3.70 (s, 3H), 1.93 (m,2H), 1.40 (m, 2H), 0.97 (t, 3H). 103 δ 7.79 (s, 1H), 7.64 (d, 1H), 7.39(d, 1H), 6.85 (s, 1H), 5.23 (br s, 1H), 4.49 (d, 2H), 4.19 (t, 2H), 3.70(s, 3H), 1.97 (m, 2H), 0.97 (t, 3H). 104 δ 8.22 (d, 1H), 7.79 (s, 1H),7.63 (d, 1H), 7.38 (d, 1H), 6.74 (d, 1H), 5.42 (br s, 1H), 4.42 (d, 2H),3.67 (s, 3H), 3.18 (m, 1H), 1.37 (d, 6H). 105 δ 8.29 (d, 1H), 7.86 (s,1H), 7.74 (d, 1H), 7.43 (d, 1H), 6.81 (d, 1H), 5.32 (br s, 1H), 4.51 (d,2H), 3.71 (s, 3H), 2.62 (s, 3H). 106 δ 7.90 (d, 1H), 7.84 (d, 1H), 7.76(d, 1H), 7.65 (d, 2H), 7.40 (d, 1H), 6.98 (d, 2H), 6.72 (d, 1H), 5.19(br s, 1H), 4.51 (d, 2H), 3.85 (s, 3H), 3.70 (s, 3H). 107 δ 7.93 (m,2H), 7.78 (d, 1H), 7.41 (d, 1H), 7.37 (m, 2H) 7.30 (m, 1H), 6.84 (d,1H), 6.75 (d, 1H), 5.19 (br s, 1H), 4.52 (d, 2H), 3.89 (s, 3H), 3.70 (s,3H). 108 δ 8.15 (d, 2H), 8.03 (d, 1H), 7, 93 (s, 1H), 7.85 (d, 2H), 7.78(d, 1H), 7.43 (d, 1H), 6.81 (d, 1H) 5.21 (br s, 1H), 4.52 (d, 2H), 3.95(s, 3H), 3.71 (s, 3H). 109 δ 7.90 (m, 2H), 7.77 (d, 1H), 7.63 (m, 2H),7.41 (d, 1H), 7.27 (m, 2H), 6.73 (d, 1H), 5.19 (br s, 1H), 4.51 (d, 2H),3.70 (s, 3H), 2.39 (s, 3H). 110 δ 7.91 (d, 2H), 7.77 (d, 1H), 7.65 (d,2H), 7.41 (d, 1H), 7.29 (m, 2H), 6.73 (d, 1H), 5.17 (br s, 1H), 4.51 (d,2H), 3.70 (s, 3H), 2.96 (m, 1H), 1.28 (d, 6H). 111 δ 7.92 (m, 2H), 7.77(d, 1H), 7.61 (m, 4H), 7.41 (m, 1H), 6.77 (d, 1H), 5.19 (br s, 1H), 4.51(d, 2H), 3.70 (s, 3H). 112 δ 7.94 (m, 3H), 7.79 (d, 1H), 7.68 (d, 1H),7.42 (d, 2H), 7.33 (m, 1H), 6.77 (d, 1H), 5.20 (br s, 1H), 4.52 (d, 2H),3.71 (s, 3H). 113 δ 8.1 (d, 1H), 7.99 (m, 2H), 7.91 (d, 1H), 7.78 (d,1H), 7.59 (m, 2H), 7.44 (d, 1H), 6.81 (d, 1H), 5.21 (br s, 1H), 4.52 (d,2H), 3.71 (s, 3H). 114 δ 8.02 (d, 1H), 7.91 (m, 3H), 7.77 (m, 3H), 7.44(d, 1H) 6.83 (d, 1H), 5.22 (br s, 1H), 4.52 (d, 2H), 3.70 (s, 3H). 115 δ7.95 (d, 1H), 7.93 (d, 1H), 7.78 (d, 1H), 7.54 (m, 2H), 7.42 (m, 2H),6.99 (m, 1H), 6.77 (d, 1H), 5.20 (br s, 1H), 4.52 (d, 2H), 3.70 (s, 3H).116 δ 7.89 (m, 2H), 7.74 (m, 3H), 7.44 (d, 1H), 7.16 (m, 2H), 6.75 (d,1H), 5.22 (br s, 1H), 4.51 (d, 2H), 3.70 (s, 3H). 117 δ 7.92 (m, 3H),7.77 (d, 1H), 7.59 (d, 1H), 7.53 (d, 1H), 7.42 (d, 1H), 6.78 (d, 1H),5.21 (br s, 1H), 4.52 (d, 2H), 3.70 (s, 3H). 118 δ 7.90 (m, 2H), 7.77(d, 1H), 7.66 (m, 1H), 7.45 (m, 2H), 7.26 (m, 1H), 6.77 (d, 1H), 5.21(br s, 1H), 4.51 (d, 2H), 3.70 (s, 3H). 126 δ 7.74 (s, 1H), 7.63 (s,1H), 7.49 (s, 1H), 7.34 (d, 2H), 5.23 (br s, 1H), 4.46 (d, 2H), 4.10 (d,2H), 3.69 (s, 3H), 1.88 (m, 2H), 0.49 (m, 2H), 0.00 (s, 9H). 127 δ 8.02(s, 1H), 7.83 (s, 2H), 7.36 (s, 2H), 5.30 (br s, 1H), 4.47 (d, 2H), 3.70(s, 3H). 128 δ 7.78 (s, 1H), 7.60 (m, 1H), 7.31 (m, 8 H), 5.32 (s, 2H),5.28 (s, 1H), 4.43 (d, 2H), 3.67 (s, 3H). 129 δ 7.80 (s, 1H), 7.69 (s,1H), 7.48 (s, 1H), 7.41 (d, 1H), 7.33 (s, 2H), 7.26 (m, 2H), 7.09 (d,1H), 5.45 (s, 2H), 5.24 (br s, 1H), 4.44 (d, 2H), 3.68 (s, 3H). 130 δ8.65 (d, 1H), 8.09 (s, 1H), 7.98 (d, 1H), 7.63 (d, 1H), 7.51 (d, 1H),5.35 (br s, 1H), 4.52 (d, 2H), 3.70 (s, 3H). 131 δ 8.84 (d, 1H), 8.27(s, 1H), 8.18 (s, 1H), 8.03 (m, 1H), 7.55 (d, 1H), 7.49 (d, 1H), 5.58(m, 1H), 4.54 (d, 2H), 3.71 (s, 3H), 2.84 (s, 3H). 132 δ 8.81 (d, 1H),8.44 (d, 2H), 8.21 (br s, 1H), 8.10 (d, 1H), 7.52 (m, 2H), 7.32 (d, 2H),5.29 (br s, 1H), 4.55 (d, 2H), 3.72 (s, 3H), 2.44 (s, 3H). 133 δ 8.83(d, 1H), 8.36 (d, 2H), 8.21 (s, 1H), 8.10 (d, 1H), 7.55 (d, 1H), 7.52(d, 1H), 7.41 (m, 1H), 7.32 (d, 1H), 5.29 (br s, 1H), 4.56 (d, 2H), 3.72(s, 3H), 2.48 (s, 3H). 134 δ 8.85 (d, 1H), 8.56 (m, 2H), 8.24 (s, 1H),8.12 (d, 1H), 7.58 (d, 1H), 7.52 (m, 4 H), 5.29 (br s, 1H), 4.56 (d,2H), 3.73 (s, 3H). 137 δ 8.58 (d, 1H), 8.08 (s, 1H), 7.94 (d, 1H), 7.46(d, 1H), 7.40 (d, 1H), 5.39 (br s, 1H), 4.52 (d, 2H), 3.71 (s, 3H), 2.31(m, 1H), 1.20 (m, 2H), 1.09 (m, 2H). 138 δ 8.92 (d, 1H), 8.16 (d, 1H),8.08 (d, 1H), 7.87 (d, 1H), 7.54 (d, 1H), 5.31 (br s, 1H), 4.54 (d, 2H),3.71 (s, 3H). 139 δ 8.56 (d, 1H), 8.10 (s, 1H), 7.95 (d, 1H), 7.52 (d,2H), 7.47 (d, 1H), 7.37 (m, 2H), 7.30 (d, 1H), 7.32 (d, 1H), 5.52 (s,2H), 5.31 (br s, 1H), 4.52 (d, 2H), 3.69 (s, 3H). 140 δ 7.71 (d, 1H),7.34 (m, 3H), 7.27 (m, 4 H), 7.03 (d, 1H), 6.51 (d, 1H), 5.12 (br s,1H), 4.37 (d, 2H), 3.66 (s, 3H). 141 δ 7.49 (m, 2H), 7.29 (m, 1H), 6.56(s, 1H), 4.49 (d, 2H), 3.91 (s, 3H), 3.68 (s, 3H). 142 δ 7.49 (d, 1H),7.44 (s, 1H), 7.26 (d, 1H), 6.51 (s, 1H), 5.23 (br s, 1H), 4.50 (d, 2H),4.14 (m, 2H), 3.69 (s, 3H), 1.75 (m, 2H), 0.87 (s, 9H). 143 δ 7.48 (d,1H), 7.43 (s, 1H), 7.25 (d, 1H), 6.51 (s, 1H), 5.23 (br s, 1H), 4.50 (d,2H), 4.11 (t, 2H), 3.69 (s, 3H), 1.79 (m, 2H), 1.24 (m, 2H), 0.86 (t,3H). 144 δ 7.48 (d, 1H), 7.43 (s, 1H), 7.25 (d, 1H), 6.51 (s, 1H), 5.24(br s, 1H), 4.50 (d, 2H), 4.08 (t, 2H), 3.69 (s, 3H), 1.84 (m, 2H), 0.85(t, 3H). 145 δ 7.94 (s, 1H), 7.83 (s, 1H), 7.70 (d, 1H), 7.42 (d, 1H),5.28 (br s, 1H), 4.50 (d, 2H), 3.71 (s, 3H). 146 δ 7.82 (s, 1H), 7.79(br s, 1H), 7.61 (d, 1H), 7.38 (d, 1H), 7.24 (d, 2H), 7.13 (d, 2H), 5.56(s, 2H), 5.23 (br s, 1H), 4.48 (d, 2H), 3.69 (s, 3H), 2.32 (s, 3H). 147δ 8.08 (d, 2H), 8.04 (s, 1H), 7.96 (br s, 1H), 7.75 (dd, 1H), 7.48-7.44(m, 3H), 5.25 (br s, 1H), 4.51 (d, 2H), 3.71 (s, 3H). 148 δ 8.20 (s,1H), 7.89 (s, 1H), 7.83 (d, 1H), 7.74 (d, 2H), 7.53 (d, 2H), 5.24 (br s,1H), 4.52 (d, 2H), 3.70 (s, 3H). 149 δ 7.77 (s, 1H), 7.72 (d, 1H), 7.65(s, 1H), 7.39 (d, 1H), 7.21 (apparent s, 4H), 5.52 (s, 2H), 5.21 (br s,1H), 4.41 (d, 2H), 3.67 (2, 3H), 2.36 (s, 3H). 150 δ 8.10 (m, 3H), 7.92(m, 3H), 7.80 (d, 1H), 6.83 (s, 1H), 5.23 (br s, 1H), 4.54 (d, 2H), 3.75(s, 3H), 2.65 (s, 3H). ^(a1)H NMR data are in ppm downfield fromtetramethylsilane. Couplings are designated by (s)—singlet, (br s)—broadsinglet, (d)—doublet, (t)—triplet, (q)—quartet, (m)—multiplet,(dd)—doublet of doublets.

Biological Examples of the Invention General Protocol for Preparing TestSuspensions for Tests A-L

The test compounds were first dissolved in acetone in an amount equal to3% of the final volume and then suspended at the desired concentration(in ppm) in acetone and purified water (50/50 mix) containing 250 ppm ofthe surfactant Trem® 014 (polyhydric alcohol esters). The resulting testsuspensions were then used in Tests A-L. Spraying a 200 ppm testsuspension to the point of run-off on the test plants was the equivalentof an application rate of 500 g/ha.

Test A

The test suspension was sprayed to the point of run-off on wheatseedlings. The following day the seedlings were inoculated with a sporedust of Erysiphe graminis f. sp. tritici (the causal agent of wheatpowdery mildew) and incubated in a growth chamber at 20° C. for 8 days,after which time disease ratings were made.

TEST B

The test suspension was sprayed to the point of run-off on wheatseedlings. The following day the seedlings were inoculated with a sporesuspension of Puccinia recondita f. sp. tritici (the causal agent ofwheat leaf rust) and incubated in a saturated atmosphere at 20° C. for24 h, and then moved to a growth chamber at 20° C. for 7 days, afterwhich time disease ratings were made.

Test C

The test suspension was sprayed to the point of run-off on wheatseedlings. The following day the seedlings were inoculated with a sporesuspension of Septoria nodorum (the causal agent of wheat glume blotch)and incubated in a saturated atmosphere at 20° C. for 48 h, and thenmoved to a growth chamber at 20° C. for 7 days, after which time diseaseratings were made.

Test D

The test suspension was sprayed to the point of run-off on wheatseedlings. The following day the seedlings were inoculated with a sporesuspension of Septoria tritici (the causal agent of wheat leaf blotch)and incubated in a saturated atmosphere at 24° C. for 48 h, and thenmoved to a growth chamber at 20° C. for 19 days, after which timedisease ratings were made.

Test E

The test suspension was sprayed to the point of run-off on wheatseedlings. The following day the seedlings were inoculated with a sporesuspension of Fusarium graminearum (the causal agent of wheat head scab)and incubated in a saturated atmosphere at 24° C. for 72H, and thenmoved to a growth chamber at 20° C. for 5 days, after which time diseaseratings were made.

Test F

The test suspension was sprayed to the point of run-off on tomatoseedlings. The following day the seedlings were inoculated with a sporesuspension of Botrytis cinerea (the causal agent of tomato Botrytis) andincubated in saturated atmosphere at 20° C. for 48 h, and then moved toa growth chamber at 24° C. for 3 additional days, after which timedisease ratings were made.

Test G

The test suspension was sprayed to the point of run-off on cucumberseedlings. The following day the seedlings were inoculated with a sporesuspension of Colletotrichum orbiculare (the causal agent of cucumberColletotrichum anthracnose) and incubated in saturated atmosphere at 20°C. for 24 h, and moved to a growth chamber at 24° C. for 5 additionaldays, after which time disease ratings were made.

Test H

The test suspension was sprayed to the point of run-off on tomatoseedlings. The following day the seedlings were inoculated with a sporesuspension of Alternaria solani (the causal agent of tomato earlyblight) and incubated in a saturated atmosphere at 27° C. for 48 h, andthen moved to a growth chamber at 20° C. for 5 days, after which timedisease ratings were made.

Test I

The test suspension was sprayed to the point of run-off on creeping bentgrass seedlings. The following day the seedlings were inoculated with aspore suspension of Rhizoctonia oryzae (the causal agent of turf brownpatch) and incubated in a saturated atmosphere at 27° C. for 48 h, andthen moved to a growth chamber at 27° C. for 3 days, after which timedisease ratings were made.

Test J

The test suspension was sprayed to the point of run-off on tomatoseedlings. The following day the seedlings were inoculated with a sporesuspension of Phytophthora infestans (the causal agent of tomato lateblight) and incubated in a saturated atmosphere at 20° C. for 24 h, andthen moved to a growth chamber at 20° C. for 4 days, after which timedisease ratings were made.

Test K

Grape seedlings were inoculated with a spore suspension of Plasmoparaviticola (the causal agent of grape downy mildew) and incubated in asaturated atmosphere at 20° C. for 24 h. After a short drying period,the test suspension was sprayed to the point of run-off on the grapeseedlings and then moved to a growth chamber at 20° C. for 6 days, afterwhich the test units were placed back into a saturated atmosphere at 20°C. for 24 h. Upon removal, disease ratings were made.

Test L

The test suspension was sprayed to the point of run-off on bluegrassseedlings. The following day the seedlings were inoculated with a sporesuspension of Pythium aphanidermatum (the causal agent of bluegrasspythium blight) and incubated in a covered saturated atmosphere at 27°C. for 48 h, and then the covers where removed and the plants left at27° C. for 3 additional days, after which time disease ratings weremade.

Results for Tests A-L are given in Table A. In the table, a rating of100 indicates 100% disease control, and a rating of 0 indicates nodisease control (relative to the controls). A dash (-) indicates no testresults. All results are for 200 ppm except where followed by an “*”,which indicates 40 ppm or “**”, which indicates 50 ppm.

TABLE A RESULTS OF BIOLOGICAL TESTS Percentage Disease Control Cmpd TestTest Test Test Test Test Test Test Test Test Test Test No. A B C D E F GH I J K L 1 100  100  100  100* 100   0 —  0  0  0 66  0 2 100  100  99 91* 100   0 — —  0  0 70  0 3 98 100  99  16* 87  0 — —  0  0 26  0 498 99 99  59* 97 37 — —  0  0 74  0 5 99 100  99 100*  0  0 — 77  0  023  0 6  99* 100*  96* 100*  68* — — — — — — — 7 100* 100*  99* 100*  0*— — — — — — — 8 100  100  99 — 92  0 100  —  0 100  99 33 9 95 99 100  — 0 29 99 —  0  0  0  0 10 98 79 82 —  0  0 25 —  0  0  0  0 11 100  100 96 — 86  0 99 —  0 93 79 87 12 98 95 98 — 98 45 91 —  0  0  0 63 13 4689 99 —  0  0 — —  0  0  0  0 14 96 98 93 —  0  0  0 —  0  0  0 80 15100* 100* 100* 100* —  0 — 33 — — — — 16  99* 100* 100* 100* — 67 —  95*— — — — 17 67  99* 100  100* —  0 — 38 — — — — 18 100*  99*  99*  98*100   0 — 70  0 89 81 98 19  99*  99*  97*  98*  99*  0* —  63* — — — —20 99 100  96 — 72  0 —  0  0  0  0  0 21  0 79  0 —  0  0 —  0  0  0  0 0 22  99*  95* 99  85* 99  0 —  0  0 50 99  94* 23  99* 100* 100*  98*99  0 —  0  0 91  99*  93* 24  96*  99*  99* —  96*  0 —  0  0  0* 83 —25 91 96 78 96 77 37 — 76  0  0 63  0 26  0 73  0 26  0  0 —  0  0 60  6 0 27 96  99*  94*  96* 93  0 —  0  0  0 76  0 28 54 88  0 86  0  0 — 28 0  0 25  0 29  78**  98**  82**  96** —   0** —  67**   0**   0**  27**  0** 30 83 98 73 90 —  0 —  0  0  0 74  0 31  0*  0*  0*  69* —  0* — 0*  0*  0*  20*  0* 32 41 80  0 88 —  0 —  0  0  0 34  0 34  97* 100* 97* 100*  98*  0 —  90*  0  0 78  0 35 76 76  0 100   0  0 —  0 — — — —36  93*  99*  99*  97* 26  0 — 78 — — — — 37  99* 100* 100* 100*  99*  0—  0 — — — — 38  98*  99* 100* 100*  96*  0 — 82 — — — — 39  99* 100* 99* 100*  91*  0 —  0 — — — — 40  99* 100*  99* 100*  13*  0* —  50* —— — — 41 99 100* 100   98*  99*  0 —  0 — — — — 42  98* 100* 100* 100*100*  0 —  0 — — — — 43 91 99 95 93 94  0 —  0 — — — — 45  99* 100* 100  99* 26  0 —  0 — — — — 46  94*  99* 99  91*  94*  0 —  0 — — — — 47 98* 100* 100*  99* 94  0 — 66 — — — — 48  65* 100*  99*  99*  94*  0* — 99* — — — — 49 79 100* 99 100*  99*  0 —  99* — — — — 50 100*  99* 100*100*  97*  0 — 55 — — — — 51  97*  99*  98* 100* —  0* —  60* — — — — 52100* 100* 100* 100* — 99 — 92 — — — — 53  98*  99*  94*  99* —  0* — 92* — — — — 54  99* 100*  99*  99* —  0* — — — — — — 55  88*  88*  92* 95* —  0* —  16* — — — — 56  89*  97*  97*  90* —  0* —  92* — — — — 57 97* 100*  87* 100* —  0* —  96* — — — — 58  98* 100* 100*  99* —  0* — 89* — — — — 59  98* 100*  99*  97* —  0* —  87* — — — — 60  98*  99* 99*  99* —  0* —  24* — — — — 61  84* 100*  99*  99* —  0* —  0* — — —— 62  99*  99* 100* 100* —  0* —  0* — — — — 63  97* 100*  99* 100* — 0* —  98* — — — — 64  99* 100* 99  93* — 16 — 62 — — — — 65  99*  99* 99* 100* —  0* —  8* — — — — 66  99* 100* 100* 100* —  0* —  96* — — —— 67  96*  99*  99* 100* —  0* —  96* — — — — 68  97* 100*  99* 100* — 0 —  86* — — — — 69  97*  92*  98*  98* —  0 — 32 — — — — 70  99*  99*100* 100* — — —  96* — — — — 71  99* 100* 100* 100* — — —  84* — — — —72  99*  99* 100* 100* —  97* —  94* — — — — 73  74*  98*  96*  98* — 95* —  14* — — — — 74 100* 100* 100* 100* —  51* —  99* — — — — 75  72* 93*  40*  91* —  20* —  61* — — — — 76  99* 100*  99* 100* —  0* —  0*— — — — 77  99* 100* 100* 100* — — —  96* — — — — 78 100*  85*  0*  90*—  33* —  0* — — — — 79  99*  99* 100*  99* —  0* — — — — — — 80  98* 98* 100* 100* —  60* —  29* — — — — 81  85*  99* 100*  99* —  81* — 97* — — — — 82  60*  0*  86* — —  0* —  7* — — — — 83 19  0  0 89 —  0—  0 — — — — 84  98* 80 92  99* — 67 — 54 — — — — 85 100*  97*  99*  99*—  0 — 86 — — — — 86  99* 100* 100*  98* —  0* —  9* — — — — 87  82*100*  97*  99* —  0* —  9* — — — — 88  95*  97* 100* 100* —  0* —  0* —— — — 89 100* 100* 100* 100* —  0 —  89* — — — — 90  0*  90*  0*  80* — 0* —  0* — — — — 91  0 85 64 97 —  0 — 33 — — — — 92 82  97*  92* 72 — 0 — 15 — — — — 93  93*  98* 100*  96* —  0 — 15 — — — — 94  0 17  0 40—  0 —  0 — — — — 95 100* 100* 100* 100* —  90* — 25 — — — — 96 100*100* 100* 100* —  0 — 59 — — — — 97  98* 100* 100* 100* —  0 — 85 — — —— 98 91  98*  90* 98 —  0 —  0 — — — — 99 82 74  0 92 — 98 —  0 — — — —100  0  0  0 40 —  0 —  0 — — — — 101  98*  99* 100*  95* —  0 —  0 — —— — 102  98*  98*  96*  98* —  0 — — — — — — 103  99*  98* 87  99* —  0— — — — — — 104 100* 100* 100* 100* —  0 — 40 — — — — 105 51 100* 100* 99* —  0 —  90* — — — — 106  98* 100* 100* 100* —  0 —  92* — — — — 107100* 100* 100*  99* — 89 —  99* — — — — 108  0 86 95  98* —  0 — 28 — —— — 109  98* 100* 100*  99* —  92* — 100* — — — — 110 100* 100* 100* 97* —  96* — 85 — — — — 111  99* 100* 100* 100* — 95 —  90* — — — — 11288  99* 100* 100* —  0 — 93 — — — — 113 92 99 100  100  — 24 —  0 — — —— 114 93 99 100  100  —  0 —  0 — — — — 115 98 99 100  100  — 32 — 96 —— — — 116 99 100  100  96 —  0 — 99 — — — — 117 98 99 100  100  — 94 —95 — — — — 118 100  100  100  100  — 40 — 99 — — — — 119 100* 100* 100*100* — 51 — 57 — — — — 120  98* 79  0  94* —  0 —  0 — — — — 121  98* 98* 100*  99* —  0 —  90* — — — — 122 100* 100* 100* 100* — 63 —  97* —— — — 123  98*  99* 100*  99* — 63 — 87 — — — — 124 100* 100* 100* 100*—  0 —  99* — — — — 126 95  98* 99  97*  0  0 —  0 — — — — 127  0  9  053 —  0 —  0 — — — — 128 29 98 82  96* —  0 —  0 — — — — 129 94 98 90 92* —  0 —  0 — — — — 130 80 67 92 96 —  0 —  0 — — — — 131  0  0  0 13—  0 —  0 — — — — 132 80  95*  98* 100* —  0 —  0 — — — — 133 94 93 93 92* —  0 —  0 — — — — 134  0 84  96* 87 —  0 —  0 — — — — 137 95 99 90*  97* —  0 — 15 — — — — 138 56 48 92 77 —  0 —  0 — — — — 139 87100*  99*  92* —  0 — 26 — — — — 140  0 32  0 96 —  0 —  0 — — — — 14196 89 82 98 —  0 —  0 — — — — 142 85 55  0 92 —  0 — 16 — — — — 143 9319  0 93 —  0 —  0 — — — — 144 97 19  0 95 —  0 —  0 — — — — 145  0  0 0 30 —  0 — 15 — — — — 146 52 93 99 93 —  0 — 22 — — — — 147 100*  99* 99* 100* — 61 — 15 — — — — 148 85  90* 90  98* — 46 —  0 — — — — 149  099 100  99 —  0 —  0 — — — — 150 71 98 100  99 —  0 — 92 — — — —

What is claimed is:
 1. A compound selected from Formula 1, N-oxides andsalts thereof,

wherein each R¹ and R² is independently H, halogen, CN, C₁-C₃ alkyl,C₁-C₃ alkoxy, C₁-C₃ haloalkyl, C₁-C₃ haloalkoxy, C₃-C₆ cycloalkyl,C₃-C₁₅ trialkylsilyl or C₃-C₁₅ halotrialkylsilyl; V is NR³; R³ is H,C₁-C₃ alkyl, C₃-C₆ cycloalkyl, C₁-C₃ haloalkyl, C₂-C₆ alkylcarbonyl,C₂-C₆ haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl or C₂-C₆haloalkoxycarbonyl; R⁴ is C₁-C₂ alkoxy, C₁-C₂ haloalkoxy, C₃-C₄cycloalkoxy, C₁-C₂ alkylamino, C₁-C₂ haloalkylamino, C₂-C₄ dialkylamino,C₂-C₄ halodialkylamino or C₃-C₄ cycloalkylamino; W is O or S; Q isCR^(6a)R^(6b) or NR⁷; Y is Z; Z is

R^(6a) is H, OH, halogen, CN, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆alkoxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylsulfonyl;R^(6b) is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkoxyalkyl, C₁-C₆alkoxy or C₁-C₆ haloalkoxy; or R^(6a) and R^(6b) are taken together withthe carbon atom to which they are attached to form a C₃-C₆ cycloalkylring or C₃-C₆ halocycloalkyl ring; R⁷ is H, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₂-C₃ alkylcarbonyl or C₂-C₃ haloalkylcarbonyl; each R¹⁴ isindependently H, halogen, cyano, hydroxy, amino, nitro, —CH(═O) or—C(═O)NH₂; or C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₃-C₆ halocycloalkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈alkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl,C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₂-C₈ alkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy,C₁-C₆ alkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆alkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈dialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈ alkylcarbonylamino, C₁-C₆alkylsulfonylamino, C₁-C₆ alkylaminosulfonyl, C₂-C₈dialkylaminosulfonyl, naphthalenyl or G^(A), each optionally substitutedwith one or more substituents independently selected from the groupconsisting of halogen, cyano, hydroxy, amino, nitro, —CH(═O), —C(═O)OH,—C(═O)NH₂, —C(R¹⁵)═N—O—R¹⁶, —C(R¹⁵)═N-R¹⁶, C₁-C₆ alkyl, C₃-C₈cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl,C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy,C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆alkynyloxy, C₃-C₆ haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀cycloalkylcarbonyloxy, C₁-C₆ alkylthio, benzylthio, C₁-C₆ haloalkylthio,C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl,C₃-C₁₀ trialkylsilyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₁-C₆haloalkylamino, C₂-C₈ halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino and G^(B); each G^(A)is independently a phenyl ring, benzyl, benzyloxy, benzoyl, phenoxy orphenylsulfonyl or a 5- or 6-membered heteroaromatic ring; each G^(B) isindependently a phenyl ring or a 5- -membered heteroaromatic ring eachoptionally substituted with one or more substituents independentlyselected from the group consisting of halogen, C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₄-C₇alkylcycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, cyano, nitro, C₁-C₆alkoxy, C₁-C₆ haloalkoxy and C₁-C₆ alkylthio; each R¹⁵ is H, C₁-C₃alkyl, C₃-C₈ cycloalkyl or C₁-C₃ haloalkyl; each R¹⁶ is H, C₁-C₃ alkyl,C₁-C₃ haloalkyl, C₂-C₃ alkylcarbonyl or C₂-C₃ haloalkylcarbonyl; and mis an integer from 1 to
 3. 2. A compound of claim 1 wherein: R¹ ishalogen, CN, C₁-C₂ alkyl, C₁-C₂ alkoxy, C₁-C₂ haloalkyl or C₁-C₂haloalkoxy; R² is H, halogen, CN, methyl or trifluoromethyl; R³ is H,C₁-C₂ alkyl, C₁-C₂ haloalkyl, C₂-C₃ alkylcarbonyl or C₂-C₃haloalkylcarbonyl; R⁴ is C₁-C₂ alkoxy, C₁-C₂ haloalkoxy, C₁-C₂alkylamino or C₂-C₄ dialkylamino; and W is O.
 3. A compound of claim 2wherein: R¹ is halogen, CN, C₁-C₂ alkyl or C₁-C₂ haloalkyl; R² is H orhalogen; R³ is H, C₁-C₂ alkyl or C₁-C₂ haloalkyl; and R⁴ is C₁-C₂ alkoxyor C₁-C₂ haloalkoxy.
 4. A compound of claim 3 wherein: each R¹⁴ isindependently C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₁-C₆ haloalkyl, C₁-C₆haloalkoxy or G^(A), each optionally substituted with one or moresubstituents independently selected from the group consisting ofhalogen, cyano, hydroxy, amino, nitro, —CH(═O), —C(═O)OH, —C(═O)NH₂,C(R¹⁵)═N—O—R¹⁶, C(R¹⁵)═N-R¹⁶, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆ alkoxy,C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy and C₃-C₁₀ trialkylsilyl.
 5. Acompound of claim 4 wherein: each G^(A) is independently phenyl or1,2,4-thiadiazole, each optionally substituted with one or moresubstituents independently selected from the group consisting ofhalogen, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy,C₃-C₈ cycloalkoxy and C₃-C₁₀ trialkylsilyl.
 6. A compound of claim 3wherein: Q is CR^(6a)R^(6b).
 7. A compound of claim 3 wherein: each R¹⁴is independently C₁-C₆ alkyl, C₃-C₈ cycloalkyl or G^(A), each optionallysubstituted with one or more substituents independently selected fromthe group consisting of halogen, cyano, hydroxy, amino, nitro, —CH(═O),—C(═O)OH, —C(═O)NH₂, C(R¹⁵)═N—O—R¹⁶, C(R¹⁵)═N-R¹⁶, C₁-C₆ alkyl, C₃-C₈cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl,C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy and C₃-C₁₀ trialkylsilyl. 8.A compound of claim 1 which is selected from the group consisting of:methylN-[[2-chloro-5-[3-[3-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl]-phenyl]methyl]carbamate;methylN-[[5-[3-(3-bromophenyl)-1H-pyrazol-1-yl]-2-chlorophenyl]-methyl]carbamate;methylN-[[2-chloro-5-[3-(4-chlorophenyl)-1H-pyrazol-1-yl]-phenyl]methyl]carbamate;methylN-[[2-chloro-5-[3-(3-chlorophenyl)-1H-pyrazol-1-yl]-phenyl]methyl]carbamate;and methylN-[[5-[3-(4-bromophenyl)-1H-pyrazol-1-yl]-2-chlorophenyl]-methyl]carbamate.9. A fungicidal composition comprising (a) a compound of claim 1; and(b) at least one other fungicide.
 10. A fungicidal compositioncomprising (1) a fungicidally effective amount of a compound of claim 1;and (2) at least one additional component selected from the groupconsisting of surfactants, solid diluents and liquid diluents.
 11. Amethod for controlling plant diseases caused by fungal plant pathogenscomprising applying to the plant or portion thereof, or to the plantseed, a fungicidally effective amount of a compound of claim
 1. 12. Thefungicidal composition of claim 9 wherein component (b) comprises atleast one compound selected from the group consisting of:acibenzolar-S-methyl, aldimorph, amisulbrom, anilazine, azaconazole,azoxystrobin, benalaxyl, benalaxyl-M, benodanil, benomyl,benthiavalicarb, benthiavalicarb-isopropyl, bethoxazin, binapacryl,biphenyl, bitertanol, bixafen, blasticidin-S, Bordeaux mixture,boscalid, bromuconazole, bupirimate, captafol, captan, carbendazim,carboxin, carpropamid, chloroneb, chlorothalonil, chlozolinate,clotrimazole, copper oxychloride, copper salts such as copper sulfateand copper hydroxide, cyazofamid, cyflufenamid, cymoxanil,cyproconazole, cyprodinil, dichlofluanid, diclocymet, diclomezine,dicloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol,dimethomorph, dimoxystrobin, diniconazole, diniconazole M, dinocap,dithianon, dodemorph, dodine, edifenphos, enestroburin, epoxiconazole,ethaboxam, ethirimol, etridiazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin chloride, fentinhydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph,fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminum, fuberidazole, furalaxyl, furametpyr, guazatine,hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadinealbesilate, iminoctadine triacetate, iodocarb, ipconazole, iprobenfos,iprodione, iprovalicarb, isoprothiolane, isotianil, kasugamycin,kresoxim-methyl, mancozeb, mandipropamid, maneb, mepanipyrim, mepronil,meptyldinocap, metalaxyl, metalaxyl-M, metconazole, methasulfocarb,metiram, metominostrobin, metrafenone, myclobutanil, naftifine,neo-asozin, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl,oxolinic acid, oxpoconazole, oxycarboxin, oxytetracycline, pefurazoate,penconazole, pencycuron, penthiopyrad, phosphorous acid and saltsthereof, phthalide, picobenzamid, picoxystrobin, piperalin, polyoxin,probenazole, prochloraz, procymidone, propamocarb,propamocarb-hydrochloride, propiconazole, propineb, proquinazid,prothiocarb, prothioconazole, pryazophos, pyraclostrobin, pyribencarb,pyributicarb, pyrifenox, pyrimethanil, pyrrolnitrin, pyroquilon,quinomethionate, quinoxyfen, quintozene, silthiofam, simeconazole,spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tecnazene,terbinafine, tetraconazole, thiabendazole, thifluzamide, thiophanate,thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolyfluanid,triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph,trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole,validamycin, valiphenal, vinclozolin, zineb, ziram, zoxamide,N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazol-4-carboxamide,N-[2-(1S,2R)-[1,1′-bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,α-[methoxyimino]-N-methyl-2-[[[1-[3-(trifluoromethyl)-phenyl]-ethoxy]imino]methyl]benzeneacetamide,2-[[[3-(2,6-dichlorophenyl)-1-methyl-2-propen-1-ylidene]amino]oxy]methyl]-α-(methoxyimino)-N-methylbenzeneacetamide,N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanamide,N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)amino]butanamide,2-[[2-fluoro-5-(trifluoromethyl)phenyl]thio]-2-[3-(2-methoxyphenyl)-2-thiazolidinylidene]acetonitrile,2-butoxy-6-iodo-3-propyl-4H-1-benzopyran-4-one,3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine,4-fluorophenylN-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]-methyl]propyl]carbamate,5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine,N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide,N-[[(cyclopropylmethoxy)amino][6-(difluoromethoxy)-2,3difluorophenyl]methylene]benzeneacetamide,N′-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide,and1-[(2-propenylthio)carbonyl]-2-(1-methylethyl)-4-(2-methylphenyl)-5-amino-1H-pyazol-3-one.13. The fungicidal composition of claim 9 wherein component (b)comprises at least one compound selected from the group consisting of:azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole,diniconazole, diniconazole-M, epoxiconazole, fenbuconazole,fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole,ipconazole, metconazole, myclobutanil, penconazole, propiconazole,prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon,triadimenol, triticonazole, uniconazole, clotrimazole, imazalil,oxpoconazole, prochloraz, pefurazoate, triflumizole, fenarimol,nuarimol, triforine and pyrifenox.
 14. The fungicidal composition ofclaim 9 wherein component (b) comprises at least one compound selectedfrom the group consisting of: benodanil, flutolanil, mepronil, fenfuram,carboxin, oxycarboxin, thifluzamide, furametpyr, penthiopyrad, bixafen,N-[2-(1S,2R)-[1,1′-bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideand boscalid.
 15. The fungicidal composition of claim 9 whereincomponent (b) comprises at least one compound selected from the groupconsisting of: azoxystrobin, enestroburin, picoxystrobin,pyraclostrobin, kresoxim-methyl, trifloxystrobin, dimoxystrobin,metominostrobin, orysastrobin,α-[methoxyimino]-N-methyl-2-[[[1-[3-(trifluoromethyl)phenyl]-ethoxy]imino]methyl]benzeneacetamide,2-[[[3-(2,6-dichlorophenyl)-1-methyl-2-propen-1-ylidene]amino]oxy]methyl]-α-(methoxyimino)-N-methylbenzeneacetamide,famoxadone, fluoxastrobin, fenamidone and pyribencarb.
 16. Thefungicidal composition of claim 9 wherein component (b) comprises atleast one compound selected from the group consisting of: copperoxychloride, copper sulfate, copper hydroxide, Bordeaux mixture,elemental sulfur, mancozeb, metiram, propineb, ferbam, maneb, thiram,zineb, ziram, folpet, captan, captafol, chlorothalonil, dichlofluanid,tolyfluanid, dodine, guazatine, iminoctadine albesilate, iminoctadinetriacetate, anilazine and dithianon.